May 7, 2025 • 30 mins
What does it really take to scale a Salesforce team from 10 to 200—without chaos? In this episode of Salesforce Hiring Edge, Josh Matthews and Josh LeQuire are joined by David Kestenberg: former CIO, Salesforce transformation leader, and 5-time Dreamforce speaker. David shares hard-won lessons on hiring for trajectory, building leadership layers, and maintaining clarity and accountability—even when you're growing at warp speed. From ‘sniper’ developers to culture-building rituals, you’ll learn how to balance technical needs with human dynamics, set your managers up for success, and create systems that scale. Packed with real-world advice for tech leaders, consulting partners, and hiring managers who want to build high-performing teams the smart way.
takeaways
- The vibe check is essential for ensuring team fit.
- Experience plays a crucial role in assessing candidates.
- Trusting managers is key to finding the right talent.
- Technical skills must align with team dynamics.
- The overall team vibe influences hiring decisions.
- Expectations should be clear during the interview process.
- A good vibe check can lead to better team cohesion.
- Understanding the 'true North' is vital for alignment.
- Hiring is not just about skills, but also about culture.
- Effective leadership involves balancing various perspectives.
Sound Bites
- "The right expectations and all of that"
- "It's about the vibe of the overall team"
- "I trust the managers that work under me"
interview process, vibe check, team dynamics, technical skills, hiring, management, leadership, organizational culture
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
David Kestenberg (00:00):
My responsibility is to do the vibe
check.
I need to say will it fit tothe overall what we're trying to
achieve today and tomorrow?
I trust the managers that workunder me and the director to get
the right people.
As far as their capabilitiesfrom a technical perspective, I
trust myself to know how to makethat fit from an overall
(00:20):
perspective for the vibe of theoverall team of what needs to
happen.
Josh Matthews (00:25):
an overall perspective for the vibe of the
overall team and what needs tohappen.
Josh LeQuire (00:30):
Welcome to Salesforce Hiring Edge, the show
for leaders who want to hiresmarter and scale faster with
Salesforce, Whether you'rebuilding a team or bringing in a
consulting partner.
We're breaking down whatactually works in the real world
.
Josh Matthews (00:37):
All right, let's get into it.
David Kestenberg is a formerCIO, tech strategist and startup
founder who's led everythingfrom M&A integrations to
Salesforce transformations.
He's built and scaled teams atReMedical, highmark Health and
multiple private equity-backedcompanies, driving growth,
cleaning up chaos and turningvision into execution.
(00:58):
He's also a five-timeDreamforce speaker and a former
IDF reconnaissance commander.
I'm just going to say I reallylove this guy.
We've had a couple hours ofconversations over the last few
weeks.
He's infinitely fascinating.
He definitely has an edge.
He's a perfect guest forSalesforce Hiring Edge.
David, welcome to the show.
David Kestenberg (01:18):
Thank you, I'm happy to be here.
Josh Matthews (01:21):
So, david, you had shared with me and Mr
LaQuire here some informationabout how you have spearheaded
enterprise Salesforcetransformations across over 20
organizations.
And look, I'll be honest withyou and with the wider audience
that while I am gifted andskilled at helping people to
(01:42):
scale teams, I am not a CIOgifted and skilled at helping
people to scale teams.
I am not a CIO.
I don't have to grow a teamfrom 10 people to 200 people in
18 months or two years, butyou've been in those kinds of
situations.
What is the number one thingthat you are afraid of when you
know you have to scale a teamsignificantly?
David Kestenberg (02:01):
Well, I would say two things.
One is always the impostersyndrome.
Am I good enough?
Am I the right man for the job?
Am I the right fit?
Can I build the right teamaround me?
Can I be the leader of leaders?
That's like the internal fearimposter syndrome, which is like
if you don't get up in themorning and say I can do better
tomorrow, you're living in thewrong body.
(02:21):
In reality, the external fearsis always the budget.
Am I solving the right problems?
Am I throwing money on the wall?
Increasing headcount?
For what purpose?
Because a lot of times scalingis not necessarily going from 10
people to 100 people.
It's not necessarily going tochange anything, it's sometimes
going from 10 to 50, butchanging roles, ranking,
(02:44):
communication, you know,internal processes, and that's
going to make the scale in theoutput.
Josh Matthews (02:50):
So you had talked about.
You had talked a little bitabout how to hire for trajectory
instead of just your immediateneed, and maybe not hiring just
to solve all of your immediateneeds, but where you're going to
be.
To solve all of your immediateneeds, but where you're going to
be, how do you help otherleaders and how have you had to
utilize your own intelligenceand strategy to figure what that
(03:12):
actually looks like?
Because we all know you couldhire 10 people.
They could show up tomorrow,but how long is it actually
going to be until they're highlyeffective?
David Kestenberg (03:21):
Right.
Well, creating the synergy Ithink it's a different type of
question, but just creating ateam for trajectory.
If I'm focusing on that, thereare basically two elements here.
Element one is usually I'm nothiring.
There's a hiring manager,there's a manager in the middle.
There's a scrum master, there'sa director.
Someone in the middle isactually hiring the individual
(03:42):
that's going to do the work.
So that individual that makesthe decision needs to work with
the right GEDQ, with the rightexpectations and all of that.
My responsibility is to do thevibe check.
Whether it's interview three orinterview two or interview four
, I need to say, will it fit tothe overall what we're trying to
achieve today and tomorrow?
(04:03):
So, to be able to do the vibecheck, I have a lot of
experience, seen a lot of peopleand been in a lot of interviews
.
I trust the managers that workunder me and the director to get
the right people as far astheir capabilities from a
technical perspective.
I trust myself to know how tomake that fit from an overall
perspective for the vibe of theoverall team, of what needs to
(04:25):
happen.
That's one side of the story.
The second side of the storyduring the vibe check, the main
thing, that I'm the main thingthat I'm checking.
The main thing that I'mchecking is where is the true
north of the individual?
Josh Matthews (04:42):
so you mean the north star, correct?
David Kestenberg (04:44):
no star, yeah true north of the individual.
So you mean the North Star,correct?
North Star?
Yeah, true north Individual,north of that individual.
That's coming to the interviewBecause some BAs want to be PMs
and some PMs want to bearchitects and some architects
want to be testers.
There are a lot of different.
Our ecosystem is so beautifulIf people are going through the
(05:05):
regular growth trajectory.
Your trajectory of growth islike you could be a BA, you'll
be a senior BA all the way toarchitect or all the way into
leadership.
You usually know you.
Usually at your mid-20s,mid-30s, you already know.
If you're just out of school,22, not even asking that
question, it's not the questionof where you want to be in 10
years, it's more of who do youthink you are?
(05:27):
Are you going into leadership?
Are you going into being a techexpert?
Once they call it, we'redoubling down on that, creating
a career, swim lane and personaldevelopment plan.
You basically attach a buddy tobe on a buddy program to help
that individual to do theonboarding.
You create a mentorship thatwill take that guy into the
(05:47):
steps that they call.
And that's the important pieceof that, Because if you're
committed to your own personaljourney, but you expose me to it
.
I know that in a year or twoyou're going to be a senior VA.
You're going to be a lead dev.
You're going to be a productowner.
I'm not going to need to hiresomeone from the outside.
You're already on track there.
You're going to be a productowner.
I'm not going to need to hiresomeone from the outside.
You're already on track there.
You're solving so many problemsthrough the system just by
(06:10):
saying this is what I want to do, I will pay for the certs.
I'm always comfortable payingfor the certs just to get the
guy go or the girl go on theirjourney.
So when you're asking how toplan for trajectory, one is the
accountability of the person andtwo is the leadership in the
middle that makes the hiringdecision needs to buy into that.
Josh LeQuire (06:31):
Follow what you're saying.
It sounds like there is in thatvibe check, you know, sort of a
culture fit assessment you'redoing looking for a growth
mentality, a learner mentality.
If you were to put weights ondifferent factors you evaluate
in a candidate, how much, whatweight would you put on the vibe
check the culture fit, thegrowth mentality, the desire to
(06:53):
learn and integrate into theteam today and tomorrow versus
technical skill versus strategicplay, and a roadmap for the
company or project or portfolioprojects you're hiring that
person in for.
David Kestenberg (07:04):
That's a really good question, Josh, and
I think you know it's reallyfascinating how to break down
the ability to predict howpeople are going to behave in
the future.
But I think in my perspectiveyou know I ran large Salesforce
teams but I'm not an architect.
Like I can't ask the rightquestion when an architect come
(07:26):
in Definitely not a MuleSoft guyor a Kapado guy.
I'm not going to be able to gotoe to toe with them.
So what I need to do is I needto do, basically, look at that,
as you know, a little bit of amilitary example, but like it's,
it's soft.
Okay.
A commander needs to know twopieces of things you need to
know how the sniper rifleoperates and it needs to know
(07:50):
the soul of the sniper.
So when you look at the sniperrifle, it's the tech stack.
Is he a health cloud?
Is he velocity?
Is he a capado?
Is he a MuleSoft?
Is he a Slack dude?
Is he an integration guy?
Is he a Tosca testing Whateverthey are?
That's that caliber range, thesoul of the sniper.
(08:10):
That's a fascinating thingBecause a sniper is like Dev
they work alone.
They sit at night with Red Bulland write code.
You know A BA needs to have.
The team needs to have theengagement, the interaction.
Let's do the solutioning.
Let's work on the documentation.
Let's do these reflectionsessions.
(08:30):
Let's do these reflectionsessions.
Let's do all those things soyou can recognize at the
individual if he's a technicalBA that behaviors as a sniper,
or he's a basketball player, ishe a swimmer that underwater?
Don't talk with anyone, justget the results I'd call the
best of the best.
Or he's a soccer player Withoutthe other 10 guys around him he
cannot play.
So when you're asking like howdo you know?
(08:52):
I'm like not everybody that Ilook going to be the MC of our
next town hall.
Some of them will not even openthe camera but they still can
be a critical piece of theorchestra and, as long as they
understand that there's agreater good, there's a higher
being of, can contribute tosociety, to my team, to the
company, and I accept that Ialso tax them with some of my
(09:16):
needs, not just cash, alsorecognition, feel good,
validation, all those.
Then we can jive.
Then there's a game.
But if there's a person thatseems like don't want to speak
that language, it seems too muchin the whatever dei space, too
much in that.
That is not comfortable with.
I'm like, okay, go work forgoogle, it's so good.
(09:37):
There's always needs fordevelopers, you know.
So that's like that's how I'mtrying to kind of put it in
frames and basically teach theofficers under me that the
directors, the managers, the theteam leads to look through.
You know, beyond the fact thatthere's a title with a rank,
with a job description, there'sa human there.
Josh Matthews (09:57):
I love that the folks listening to this show.
They may be listening right nowand going like, yeah, I do need
to scale.
I need to add 20 people in thenext six months.
I'm working with a client rightnow.
They need to add five people inthe next six weeks.
Okay, we can do that, but whenwe're talking really large scale
, I got to spin it up.
Spin it up fast.
(10:17):
What kind of structure do youprovide to these directors
beneath you Seeing what'snecessary?
And, more importantly, moreimportantly, what advice would
you have for the peoplelistening to this program?
Like what are the one, two orthree takeaways that they should
really be keeping top of mindwhen they're advising their
(10:38):
managers and directors belowthem for making this happen,
because it's got to happen?
What would you tell them?
David Kestenberg (10:44):
Well.
So I think this answer is goingto be a little bit less
inspiring than snipers andswimmers.
I think there are frameworks ofwork.
Okay, so if we are anorganization that is committed
to agile, then you're buildingscrum teams.
It's very, very simple.
You know, everyone in the scrumteam has a role.
Are you a BA, are you a dev,are you a scrum master, are you
(11:07):
a PM, whatever coach you know?
So you're filling slots.
So when you're thinking about,you know, we had an amazing
opportunity to build a productin Highmark and we had to
rapidly hire a lot of people Idon't know, 70 people over three
months, some version of likeinsane during COVID, from all
times in life, during COVID todo that boost.
(11:30):
So we made a hug home and wewere like, okay, it's fine, we
need 20 developers and 15 BAsand this and that, but we're not
.
We actually need to trust ourleadership and say, okay, this
is six scrum teams.
Each scrum team has two leaders, one scrum master, one product
owner.
Great, let's get those two andlet them build the other four,
(11:52):
the other six, so delegate.
So, yes, you take the redaccounts to yourself, ownership
of the problems and you delegatethe green, everything that is
working.
You push down because everybodycan do that Everything.
That is a problem.
You ask to be involved.
You are present in the hardconversations as a leader, but
(12:19):
we are talking about pre-problem.
It's okay, we have 30 racksthat we have to fill and time to
market is what you said sixweeks or 10 weeks on 20 people.
You have to break it down toteams.
You have to allow a middleleadership and junior leadership
, team leaders to be involved inthe hiring process, not
necessarily the be involved inthe hiring process, not
necessarily the job descriptionor the end goal, the individual
interviews and say, okay, you'regoing to be working with me.
I have a certain style.
(12:39):
Are you a good fit?
No, okay, you're going to workwith Josh.
Josh has a different style,enjoy him.
You know it's not necessarilythat the individual that is
going to an interview going toget a yes or no based on the
first or second interaction withthe company you know.
So you need to have thatversatility.
Now, the main thing with scalingis that magic spreadsheet is
(13:02):
that it's a holy grail.
Everybody needs to, becauseyou're doing second interview
and third interview andtechnical interview and then
super technical interview andall those things.
You need to have the holy grailof one centralized location,
that you have the summaries ofall the interviews, the feedback
from the people and then, ifit's going to the next one and
(13:23):
next round, they need to keepupdate the same place.
So I usually had one of one ofthe quarterbacks of those
sessions updating that andmaking sure that this is
happening, because it wascritical that was.
I would say that was number oneadvice.
Josh Matthews (13:38):
That's intense stuff.
Have you utilized like ascorecard or segmented out who's
going to cover what?
I think I saw in some of ourconversation notes around having
look, these people are checkingfor vibe or culture.
These people are checking fortechnical competency.
But let's say you've got Jimover here and Sally over there.
(13:59):
They decide the vibe check'snot good for Jim's team, could
be good for Sally's team.
But how do they convey beyondjust their own personal
perspective?
Well, so, josh, let's start withthe simplest thing Are you
using a scorecard or somethinglike that?
David Kestenberg (14:14):
Yes, we do use the nine box and we use the
scorecards and that, but that'snot for the interview.
That's later on in the three,six and nine months checkups on
the quality of the individual Inthe interview.
To be very, very honest, fightcheck is interview three.
You need to first pass thebarriers of what is expected
from the job and after thatwe'll determine what kind of
(14:37):
personality you have.
If you're not passing theminimum barrier of you know you
can do mule self-integration oryou can do heavy workflows on
velocity or whatever it is, thenit doesn't matter that you're
cool the fact that you can, youknow, work on cars or whatever
it is then it doesn't matterthat you're cool the fact that
you can, you know, work on carsor ride boats or be an amazing
chef or play different musicinstruments that none of us ever
(15:01):
seen.
Josh Matthews (15:02):
Stop talking about me, David.
Stop talking about me, yesexactly you know.
David Kestenberg (15:06):
So I would say that, yes, there is a method.
You start with the technicaland the hiring managers.
If it's the same person, great,and if not, then you start with
the technical and then it'sgoing to the hiring manager.
Okay.
Josh Matthews (15:20):
Let me ask you this You've said in the past
that culture is reinforcedthrough systems and rituals.
Right, right?
What do you mean by that?
David Kestenberg (15:29):
So my two favorite rituals are the Friday
call, which is an organizationlevel call.
So it's if I have two threedirectors under me, or two three
managers under me and I'm thedirector, it's the entire org
that is working for me.
So it's a hands on that is nota town hall.
That has a certain cadencewithin that Friday meeting.
(15:53):
That includes, you know,acknowledgement and a guest
speaker and some music.
It's a cultural, a lot ofdifferent things in that Friday
call but it's basically ahands-on.
That number one highlight isthe essay Situation Awareness.
It's telling the truth in frontof everybody about what's going
on, if we are on the mountainor to the mountain, whether we
(16:16):
are at the end of the sprint orbeginning of the sprint, close
to deployment or far fromdeployment, saying everything
that needs to happen, sayingwhat they need to hear and
allowing a lot of feedback tocome and be an open conversation
.
When I'm saying acknowledgement, it's not some manager
appointing some dude that didthe deployment.
That's not acknowledgement,that's just badges.
(16:38):
Acknowledgement is a teammember recognizing a different
team member on action that theydid.
It's like who find the barriers?
You know, show me a smallsuccess that happened but
someone else did.
Don't do I did great, don't dolike some manager appointing
some dude.
You create collaborationbetween the different teams.
So our ritual is every Fridaycall start with the MVP picking
(17:01):
the song that we're going to puton.
Before you know, the first twoand a half minutes of the
meeting is like everybodyjoining because there's 50
people.
So the songs some dude pickMetallica and some dude pick
some Indian music and some dudepick some Indian music and some
dude pick some Israeli music asthe only Israeli on the court,
and they're already exposed andbecoming themselves.
Then we move into theacknowledgement.
(17:21):
They already start recognizingand high-fiving each other.
They've created the right vibeand the right conversation.
Then you move into other piecesof that, then the situation
awareness, obviouslyhousekeeping at the end and that
.
So that Friday ritual is greatbecause things are flushing out
in that Friday.
Then Monday morning I sit withmy leaders and we say, okay,
(17:47):
here's the three objectives thatwe need to do for the week.
Those are what important to me.
Do we understand each other?
Do you see things the way thatI see them?
Do you understand thepriorities?
Do you understand the how andthe why?
Interesting.
Josh LeQuire (18:00):
So it sounds like, david, you've got an opening
and a closing almost to a weekright.
You've got your opening ritualson Monday, your closing rituals
on Friday.
Friday is celebrating success.
Monday is all right, let's getfocused.
David Kestenberg (18:12):
And it's a lot more than that, because Friday
you go to the team meeting, butThursday you're doing the
dashboards.
You're doing the dashboardsbecause there's also going to be
an exec meeting on Friday, notjust a team meeting on Friday.
So it's moving in a certain way, but I want to put the
spotlight on full team, not townhall, not something that
(18:35):
everybody needs to dress up,something that everybody's
coming with their lives,something that everybody's happy
and smiling to see each other,that type of meeting.
And then Monday it's a lot morebrief.
It could be a call, it could bean email, it could be guys,
very clear, regular week, threeobjectives.
All right, kill it, let me know, control your sector.
If you have problems, let meknow, I'm here, that's it, you
(18:56):
know.
It could be.
It could be five minutes on onmonday, but it's important to
invest the time on friday withthe team.
Let them go to the weekendfeeling appreciated, but for
real, by their teammates, not bysome dude, some suit like by
the teammate.
Josh LeQuire (19:17):
Feeling seen is really really important to want
to come back on Monday.
The theme of collaboration hereis phenomenal.
I share an opinion here withyou that I'm sure you have, that
when you foster that level ofrecognition among teammates,
that positive reinforcement loop, just compounds and compounds,
and compounds.
It brings people closertogether.
It helps to achieve resultsvery effectively.
(19:38):
What are some other ways tofoster that kind of
collaboration day to day, notjust on Fridays, with
recognizing a team member?
David Kestenberg (19:47):
You know, I think that it's very important
to bring yourself and your wholeself into the story, and
sometimes it's difficult.
Sometimes people are more.
You know, not everybody is anextrovert, introvert.
I don't want to talk about mydad, my kids, my dad.
(20:08):
Some people are verycomfortable doing that.
Everybody has something thatthey really like to talk about
and once we make them feelcomfortable, they will.
And it can be.
You know, we just had Passovera week ago.
Talk about freedom from aJewish perspective.
It can be a part of a meetingbecause it's, you know, it's
inspiring.
And then, you know, because ITis super diverse, you get to
(20:33):
have all you know, the indianculture coming in with the wally
and with cricket, and obviously, people that actually
understand soccer, not likeamericans.
And so if there was a gameyesterday, there is not a
problem to open a meeting withtop of mind have.
Have you seen Barca yesterday?
Yes, no, was it cool?
(20:54):
Move on.
And when you bring yourself andit's, you lower the walls,
we're already connected onsomething.
I know that he's a cow guybecause he keep wearing all
those brands.
Great, now we have something tojudge on as people and not, as
you know, bricks Like yeah, I'mba on this project and this is
(21:15):
all the things that you willhear from me.
Otherwise I'm a bot, you know.
So, humanizing the individualopening the door, and it's
dangerous, I have to say.
You know, hl don't like it.
Josh LeQuire (21:26):
They are not sometimes people bring a little
too much through the door well,yes, no, no.
David Kestenberg (21:31):
You know we need to have boundaries in the
way that we do that.
But when I started those Fridaycalls and then COVID hits, we
had to talk about difficultthings.
People were afraid.
People had both financialcrisis and health crisis and
isolation.
Now everybody wants to workfrom home.
But you know, five years ago,definitely for people that were
(21:54):
at that time 22, 24, that wasit's big or people that got
locked in the house, you know,after working in the office for
15 years, opening the door totalk about those challenges,
yeah, you're kind of walkingthis HR line that they might say
, hey, you are, you can be aliability here and I'm like, as
(22:14):
long as it's all in positivenote, it will increase
productivity.
Josh Matthews (22:18):
The thing that I keep hearing is accountability
and zero ambiguity, like thosetwo things combined with
vulnerability.
I'd say those three things seemto be echoing through you, and
I don't think I'm wrong here.
I think this is what you'resaying.
So when we look at Thursday,it's your dashboards, friday,
(22:39):
it's your big meeting, it's yourbig vibe meeting, right, and
it's a hoorah.
But at the end of the day, youcan't have ambiguity in these
situations and it's reallyimpossible to scale without
trust, and I had the fortunateopportunity to spend a couple
hours in the last month or sochatting with someone who
(23:00):
reported directly to you Verybright, very smart.
Are we dropping?
David Kestenberg (23:04):
names.
Josh Matthews (23:07):
No, we're not going to drop names on the show.
David Kestenberg (23:09):
We'll see, he's a call guy he's a car slash
boat guy.
Yes, yeah.
Josh Matthews (23:15):
Yeah, axar, highly intelligent, very bright,
and it made so much sense to mewhen we, when you and I talked
and and then, after alreadyhaving spoken and spent some
time with Axar, it's like, well,yeah, if you've got people like
Axar on your team, of courseyou can feel confident in
delegating, but you're the onewho has to pick those
(23:39):
lieutenants under you thosedirectors?
What do you do, like, aside fromlike the tech check and the
vibe check?
I get that because you and Ithink we're very similar
personality profiles.
You do a different profilesystem than I do, but I
correlated it and we'repractically the same.
We're very different peoplewith very different experiences,
but we kind of approach theworld, I think, similarly.
(23:59):
We see the same information, wemake decisions kind of based on
the same things.
When you personally have tobuild your team of lieutenants
or your team of directors andmanagers under you, that's
different than scaling 70 peoplein three months right, I need
three to six people and I needthem very quickly.
I need three to six people andI need them very quickly.
I'm just curious what do you dofirst?
(24:20):
Do you check your network?
You call your favoriterecruiter, you post an ad on
LinkedIn?
No, no, only network Onlynetwork.
David Kestenberg (24:28):
We're old enough to be able to say, for
that intimate role that isreporting directly to me and
need to be one of four, maximumfive people, then it's most
likely people that I alreadyknow.
It can be that they weremanagers before and now I'm
(24:49):
ready for them to be directors.
So you know, when I moved fromdifferent places, people that
were maybe a little bit lowermoved up and now reporting
directly to me, but it's usuallywithin that clan, within that
group of people that I know.
But I want to touch on, well,two things.
One, when you were talking aboutthat vulnerability element and
(25:10):
lack of ambiguity Right, Idisagree as strongly as I can
about the ambiguity.
You can be extremely clearabout your ambiguity, extremely
clear.
You can come to your team andsay here, guys, here's the
situation.
We don't know if the client isgoing to do A or B and we will
not know.
In the next 27 days we willneed to operate without knowing
(25:33):
that situation and maybe it'sgoing to be A, b or C, but we
will not know.
And I need you to be agile andvigilant and all those amazing
adjectives, but it's stillambiguity.
But it's clear that it's that.
Josh Matthews (25:48):
That's still zero ambiguity as far as I'm
concerned.
I mean, these guys are running200 miles per hour around the
track.
They've got a plan A, plan B,plan C, like you've got to plan
for alternatives.
So that's fair enough.
But I think when we're talkingto our team members and we're
trying to understand what'sgoing on with them, the clients
can be ambiguous.
Right, there's 10 other peopleover in that firm.
(26:10):
They're all meeting, they'retrying to come up with some
ideas, they're waiting forinformation from us.
Then it's a back and forth loopand we're going to get it.
But when we're talking to thosemanagers under us, when we're
talking to those directors, Ourcore value is not changing.
David Kestenberg (26:24):
We will always do the best we can the fastest
we can at the lowest budget thatwe can.
They understand that.
Josh Matthews (26:30):
But there's still zero ambiguity.
It's like don't feed mebullshit, don't feed me bullshit
, Don't tell me you don't know.
If it's something that youcould find out, go find it out.
It's not like don't find outjust because you don't feel like
finding it out.
David Kestenberg (26:46):
Go find it out .
You know what.
Let's connect that to how Ipick my people.
So part of how I pick my peoplethat's the part one is that.
Part two is I need to be ableto tell them that sounds like a
you problem.
Because that sounds like a youproblem is like I trust you, I
believe in you, control yoursector, solve it.
And if you don't need that, if,if you cannot raise a flare, I
will be there before the flareis going down.
You know that's.
(27:07):
But someone that cannot acceptit sounds like a you problem and
and will freak out, probablycannot be in the immediate
circle.
So there's a couple of filterslike that and in my head I have,
you know, a color system andobviously green is the account
management and the vendormanagement, the money side, the
(27:31):
budget of labor, budget oflicenses, budget, that.
So there's a green guy and he'sgoing to do that.
There's always in the fivepeople team.
There's always going to be thatguy.
And then there's going to be adev guy.
It doesn't need to be a VP ofengineering, it needs to be
someone that can take zero toone, that can drive the team
into something.
That was not there yesterdayand now it's there, that guy.
(27:51):
And then there needs to besomeone that can speak with
everybody, that can go to theproduct team, that can go to
client side and they can go tothe dev and be kind to all of
them, understand, speak all thelanguages and be able to do that
the Minister of Foreign Affairsoffice.
So when I'm sitting and I'mmaking my Israeli salad to my
(28:13):
media team and we're sitting andeating and talking, you can
look around the table and youwill see that they can all bond,
but they are extremelydifferent because they have
their sectors.
There's overlapping between thesectors.
Obviously, the dev guy needs tobe on the same page with the
money guy and the money guyneeds to be on the same page
with the guy that makes thepromises, the solution guy.
But they are very, verydifferent and for me it's like
(28:36):
there are four or five seatsthat we need to fill and if we
do that, under them they willknow how to build those
lieutenants and below thelieutenants, and that they will
know how to scale those teams,because the machine has the
logistic element, the core, youknow, the fighting force and
then the rest of the fluff thatwe need to have, so it's's.
Josh LeQuire (28:57):
I hope it makes sense that it doesn't well, I
think, david, what I'm hearingis like you, you seem.
I don't know if this is innateor you've developed this through
experience working, you know,kind of in the civilian sector,
or if this came through some ofyour military training.
David Kestenberg (29:10):
It's more of a ceo behavior than uh, yeah, uh
than a lieutenant or I happen tobe a major, but like it's more
of a CEO perspective, I need theCFO to deal with the money.
It happens to be a manager thatjust deal with the 50 people
budget.
Josh LeQuire (29:25):
This is great because, david, you're right.
I think what it sounds likeyou're kind of leaning into is
what kind of roles do I need,who's the best fit for that role
, and how can we, day by day,develop people in those roles
and develop people to rely oneach other for their individual,
unique talents across the team?
Josh Matthews (29:43):
Ladies and gentlemen, this has been
Salesforce Hiring Edge withDavid Kestenberg, and if you'd
like to connect with David, youshould.
He's on LinkedIn, kestenberg,k-e-s-t-e-n and it'll come right
up.
That's B-E-R-G.
By the way, david, thank you somuch for being on our program
today.
Happy to be here and, by theway, you're welcome back.
In fact, I think you're comingback for another episode.
David Kestenberg (30:05):
I hope so, if you'll help me.
Josh Matthews (30:07):
Absolutely.
We'd love to have you on.
Thanks so much, david and Josh.
Great questions today.
Thanks everybody.
My responsibility is to do the vibe
check.
I need to say will it fit tothe overall what we're trying to
achieve today and tomorrow?
I trust the managers that workunder me and the director to get
the right people.
As far as their capabilitiesfrom a technical perspective, I
trust myself to know how to makethat fit from an overall
(00:20):
perspective for the vibe of theoverall team of what needs to
happen.
Josh Matthews (00:25):
an overall perspective for the vibe of the
overall team and what needs tohappen.
Josh LeQuire (00:30):
Welcome to Salesforce Hiring Edge, the show
for leaders who want to hiresmarter and scale faster with
Salesforce, Whether you'rebuilding a team or bringing in a
consulting partner.
We're breaking down whatactually works in the real world
.
Josh Matthews (00:37):
All right, let's get into it.
David Kestenberg is a formerCIO, tech strategist and startup
founder who's led everythingfrom M&A integrations to
Salesforce transformations.
He's built and scaled teams atReMedical, highmark Health and
multiple private equity-backedcompanies, driving growth,
cleaning up chaos and turningvision into execution.
(00:58):
He's also a five-timeDreamforce speaker and a former
IDF reconnaissance commander.
I'm just going to say I reallylove this guy.
We've had a couple hours ofconversations over the last few
weeks.
He's infinitely fascinating.
He definitely has an edge.
He's a perfect guest forSalesforce Hiring Edge.
David, welcome to the show.
David Kestenberg (01:18):
Thank you, I'm happy to be here.
Josh Matthews (01:21):
So, david, you had shared with me and Mr
LaQuire here some informationabout how you have spearheaded
enterprise Salesforcetransformations across over 20
organizations.
And look, I'll be honest withyou and with the wider audience
that while I am gifted andskilled at helping people to
(01:42):
scale teams, I am not a CIOgifted and skilled at helping
people to scale teams.
I am not a CIO.
I don't have to grow a teamfrom 10 people to 200 people in
18 months or two years, butyou've been in those kinds of
situations.
What is the number one thingthat you are afraid of when you
know you have to scale a teamsignificantly?
David Kestenberg (02:01):
Well, I would say two things.
One is always the impostersyndrome.
Am I good enough?
Am I the right man for the job?
Am I the right fit?
Can I build the right teamaround me?
Can I be the leader of leaders?
That's like the internal fearimposter syndrome, which is like
if you don't get up in themorning and say I can do better
tomorrow, you're living in thewrong body.
(02:21):
In reality, the external fearsis always the budget.
Am I solving the right problems?
Am I throwing money on the wall?
Increasing headcount?
For what purpose?
Because a lot of times scalingis not necessarily going from 10
people to 100 people.
It's not necessarily going tochange anything, it's sometimes
going from 10 to 50, butchanging roles, ranking,
(02:44):
communication, you know,internal processes, and that's
going to make the scale in theoutput.
Josh Matthews (02:50):
So you had talked about.
You had talked a little bitabout how to hire for trajectory
instead of just your immediateneed, and maybe not hiring just
to solve all of your immediateneeds, but where you're going to
be.
To solve all of your immediateneeds, but where you're going to
be, how do you help otherleaders and how have you had to
utilize your own intelligenceand strategy to figure what that
(03:12):
actually looks like?
Because we all know you couldhire 10 people.
They could show up tomorrow,but how long is it actually
going to be until they're highlyeffective?
David Kestenberg (03:21):
Right.
Well, creating the synergy Ithink it's a different type of
question, but just creating ateam for trajectory.
If I'm focusing on that, thereare basically two elements here.
Element one is usually I'm nothiring.
There's a hiring manager,there's a manager in the middle.
There's a scrum master, there'sa director.
Someone in the middle isactually hiring the individual
(03:42):
that's going to do the work.
So that individual that makesthe decision needs to work with
the right GEDQ, with the rightexpectations and all of that.
My responsibility is to do thevibe check.
Whether it's interview three orinterview two or interview four
, I need to say, will it fit tothe overall what we're trying to
achieve today and tomorrow?
(04:03):
So, to be able to do the vibecheck, I have a lot of
experience, seen a lot of peopleand been in a lot of interviews
.
I trust the managers that workunder me and the director to get
the right people as far astheir capabilities from a
technical perspective.
I trust myself to know how tomake that fit from an overall
perspective for the vibe of theoverall team, of what needs to
(04:25):
happen.
That's one side of the story.
The second side of the storyduring the vibe check, the main
thing, that I'm the main thingthat I'm checking.
The main thing that I'mchecking is where is the true
north of the individual?
Josh Matthews (04:42):
so you mean the north star, correct?
David Kestenberg (04:44):
no star, yeah true north of the individual.
So you mean the North Star,correct?
North Star?
Yeah, true north Individual,north of that individual.
That's coming to the interviewBecause some BAs want to be PMs
and some PMs want to bearchitects and some architects
want to be testers.
There are a lot of different.
Our ecosystem is so beautifulIf people are going through the
(05:05):
regular growth trajectory.
Your trajectory of growth islike you could be a BA, you'll
be a senior BA all the way toarchitect or all the way into
leadership.
You usually know you.
Usually at your mid-20s,mid-30s, you already know.
If you're just out of school,22, not even asking that
question, it's not the questionof where you want to be in 10
years, it's more of who do youthink you are?
(05:27):
Are you going into leadership?
Are you going into being a techexpert?
Once they call it, we'redoubling down on that, creating
a career, swim lane and personaldevelopment plan.
You basically attach a buddy tobe on a buddy program to help
that individual to do theonboarding.
You create a mentorship thatwill take that guy into the
(05:47):
steps that they call.
And that's the important pieceof that, Because if you're
committed to your own personaljourney, but you expose me to it
.
I know that in a year or twoyou're going to be a senior VA.
You're going to be a lead dev.
You're going to be a productowner.
I'm not going to need to hiresomeone from the outside.
You're already on track there.
You're going to be a productowner.
I'm not going to need to hiresomeone from the outside.
You're already on track there.
You're solving so many problemsthrough the system just by
(06:10):
saying this is what I want to do, I will pay for the certs.
I'm always comfortable payingfor the certs just to get the
guy go or the girl go on theirjourney.
So when you're asking how toplan for trajectory, one is the
accountability of the person andtwo is the leadership in the
middle that makes the hiringdecision needs to buy into that.
Josh LeQuire (06:31):
Follow what you're saying.
It sounds like there is in thatvibe check, you know, sort of a
culture fit assessment you'redoing looking for a growth
mentality, a learner mentality.
If you were to put weights ondifferent factors you evaluate
in a candidate, how much, whatweight would you put on the vibe
check the culture fit, thegrowth mentality, the desire to
(06:53):
learn and integrate into theteam today and tomorrow versus
technical skill versus strategicplay, and a roadmap for the
company or project or portfolioprojects you're hiring that
person in for.
David Kestenberg (07:04):
That's a really good question, Josh, and
I think you know it's reallyfascinating how to break down
the ability to predict howpeople are going to behave in
the future.
But I think in my perspectiveyou know I ran large Salesforce
teams but I'm not an architect.
Like I can't ask the rightquestion when an architect come
(07:26):
in Definitely not a MuleSoft guyor a Kapado guy.
I'm not going to be able to gotoe to toe with them.
So what I need to do is I needto do, basically, look at that,
as you know, a little bit of amilitary example, but like it's,
it's soft.
Okay.
A commander needs to know twopieces of things you need to
know how the sniper rifleoperates and it needs to know
(07:50):
the soul of the sniper.
So when you look at the sniperrifle, it's the tech stack.
Is he a health cloud?
Is he velocity?
Is he a capado?
Is he a MuleSoft?
Is he a Slack dude?
Is he an integration guy?
Is he a Tosca testing Whateverthey are?
That's that caliber range, thesoul of the sniper.
(08:10):
That's a fascinating thingBecause a sniper is like Dev
they work alone.
They sit at night with Red Bulland write code.
You know A BA needs to have.
The team needs to have theengagement, the interaction.
Let's do the solutioning.
Let's work on the documentation.
Let's do these reflectionsessions.
(08:30):
Let's do these reflectionsessions.
Let's do all those things soyou can recognize at the
individual if he's a technicalBA that behaviors as a sniper,
or he's a basketball player, ishe a swimmer that underwater?
Don't talk with anyone, justget the results I'd call the
best of the best.
Or he's a soccer player Withoutthe other 10 guys around him he
cannot play.
So when you're asking like howdo you know?
(08:52):
I'm like not everybody that Ilook going to be the MC of our
next town hall.
Some of them will not even openthe camera but they still can
be a critical piece of theorchestra and, as long as they
understand that there's agreater good, there's a higher
being of, can contribute tosociety, to my team, to the
company, and I accept that Ialso tax them with some of my
(09:16):
needs, not just cash, alsorecognition, feel good,
validation, all those.
Then we can jive.
Then there's a game.
But if there's a person thatseems like don't want to speak
that language, it seems too muchin the whatever dei space, too
much in that.
That is not comfortable with.
I'm like, okay, go work forgoogle, it's so good.
(09:37):
There's always needs fordevelopers, you know.
So that's like that's how I'mtrying to kind of put it in
frames and basically teach theofficers under me that the
directors, the managers, the theteam leads to look through.
You know, beyond the fact thatthere's a title with a rank,
with a job description, there'sa human there.
Josh Matthews (09:57):
I love that the folks listening to this show.
They may be listening right nowand going like, yeah, I do need
to scale.
I need to add 20 people in thenext six months.
I'm working with a client rightnow.
They need to add five people inthe next six weeks.
Okay, we can do that, but whenwe're talking really large scale
, I got to spin it up.
Spin it up fast.
(10:17):
What kind of structure do youprovide to these directors
beneath you Seeing what'snecessary?
And, more importantly, moreimportantly, what advice would
you have for the peoplelistening to this program?
Like what are the one, two orthree takeaways that they should
really be keeping top of mindwhen they're advising their
(10:38):
managers and directors belowthem for making this happen,
because it's got to happen?
What would you tell them?
David Kestenberg (10:44):
Well.
So I think this answer is goingto be a little bit less
inspiring than snipers andswimmers.
I think there are frameworks ofwork.
Okay, so if we are anorganization that is committed
to agile, then you're buildingscrum teams.
It's very, very simple.
You know, everyone in the scrumteam has a role.
Are you a BA, are you a dev,are you a scrum master, are you
(11:07):
a PM, whatever coach you know?
So you're filling slots.
So when you're thinking about,you know, we had an amazing
opportunity to build a productin Highmark and we had to
rapidly hire a lot of people Idon't know, 70 people over three
months, some version of likeinsane during COVID, from all
times in life, during COVID todo that boost.
(11:30):
So we made a hug home and wewere like, okay, it's fine, we
need 20 developers and 15 BAsand this and that, but we're not
.
We actually need to trust ourleadership and say, okay, this
is six scrum teams.
Each scrum team has two leaders, one scrum master, one product
owner.
Great, let's get those two andlet them build the other four,
(11:52):
the other six, so delegate.
So, yes, you take the redaccounts to yourself, ownership
of the problems and you delegatethe green, everything that is
working.
You push down because everybodycan do that Everything.
That is a problem.
You ask to be involved.
You are present in the hardconversations as a leader, but
(12:19):
we are talking about pre-problem.
It's okay, we have 30 racksthat we have to fill and time to
market is what you said sixweeks or 10 weeks on 20 people.
You have to break it down toteams.
You have to allow a middleleadership and junior leadership
, team leaders to be involved inthe hiring process, not
necessarily the be involved inthe hiring process, not
necessarily the job descriptionor the end goal, the individual
interviews and say, okay, you'regoing to be working with me.
I have a certain style.
(12:39):
Are you a good fit?
No, okay, you're going to workwith Josh.
Josh has a different style,enjoy him.
You know it's not necessarilythat the individual that is
going to an interview going toget a yes or no based on the
first or second interaction withthe company you know.
So you need to have thatversatility.
Now, the main thing with scalingis that magic spreadsheet is
(13:02):
that it's a holy grail.
Everybody needs to, becauseyou're doing second interview
and third interview andtechnical interview and then
super technical interview andall those things.
You need to have the holy grailof one centralized location,
that you have the summaries ofall the interviews, the feedback
from the people and then, ifit's going to the next one and
(13:23):
next round, they need to keepupdate the same place.
So I usually had one of one ofthe quarterbacks of those
sessions updating that andmaking sure that this is
happening, because it wascritical that was.
I would say that was number oneadvice.
Josh Matthews (13:38):
That's intense stuff.
Have you utilized like ascorecard or segmented out who's
going to cover what?
I think I saw in some of ourconversation notes around having
look, these people are checkingfor vibe or culture.
These people are checking fortechnical competency.
But let's say you've got Jimover here and Sally over there.
(13:59):
They decide the vibe check'snot good for Jim's team, could
be good for Sally's team.
But how do they convey beyondjust their own personal
perspective?
Well, so, josh, let's start withthe simplest thing Are you
using a scorecard or somethinglike that?
David Kestenberg (14:14):
Yes, we do use the nine box and we use the
scorecards and that, but that'snot for the interview.
That's later on in the three,six and nine months checkups on
the quality of the individual Inthe interview.
To be very, very honest, fightcheck is interview three.
You need to first pass thebarriers of what is expected
from the job and after thatwe'll determine what kind of
(14:37):
personality you have.
If you're not passing theminimum barrier of you know you
can do mule self-integration oryou can do heavy workflows on
velocity or whatever it is, thenit doesn't matter that you're
cool the fact that you can, youknow, work on cars or whatever
it is then it doesn't matterthat you're cool the fact that
you can, you know, work on carsor ride boats or be an amazing
chef or play different musicinstruments that none of us ever
(15:01):
seen.
Josh Matthews (15:02):
Stop talking about me, David.
Stop talking about me, yesexactly you know.
David Kestenberg (15:06):
So I would say that, yes, there is a method.
You start with the technicaland the hiring managers.
If it's the same person, great,and if not, then you start with
the technical and then it'sgoing to the hiring manager.
Okay.
Josh Matthews (15:20):
Let me ask you this You've said in the past
that culture is reinforcedthrough systems and rituals.
Right, right?
What do you mean by that?
David Kestenberg (15:29):
So my two favorite rituals are the Friday
call, which is an organizationlevel call.
So it's if I have two threedirectors under me, or two three
managers under me and I'm thedirector, it's the entire org
that is working for me.
So it's a hands on that is nota town hall.
That has a certain cadencewithin that Friday meeting.
(15:53):
That includes, you know,acknowledgement and a guest
speaker and some music.
It's a cultural, a lot ofdifferent things in that Friday
call but it's basically ahands-on.
That number one highlight isthe essay Situation Awareness.
It's telling the truth in frontof everybody about what's going
on, if we are on the mountainor to the mountain, whether we
(16:16):
are at the end of the sprint orbeginning of the sprint, close
to deployment or far fromdeployment, saying everything
that needs to happen, sayingwhat they need to hear and
allowing a lot of feedback tocome and be an open conversation
.
When I'm saying acknowledgement, it's not some manager
appointing some dude that didthe deployment.
That's not acknowledgement,that's just badges.
(16:38):
Acknowledgement is a teammember recognizing a different
team member on action that theydid.
It's like who find the barriers?
You know, show me a smallsuccess that happened but
someone else did.
Don't do I did great, don't dolike some manager appointing
some dude.
You create collaborationbetween the different teams.
So our ritual is every Fridaycall start with the MVP picking
(17:01):
the song that we're going to puton.
Before you know, the first twoand a half minutes of the
meeting is like everybodyjoining because there's 50
people.
So the songs some dude pickMetallica and some dude pick
some Indian music and some dudepick some Indian music and some
dude pick some Israeli music asthe only Israeli on the court,
and they're already exposed andbecoming themselves.
Then we move into theacknowledgement.
(17:21):
They already start recognizingand high-fiving each other.
They've created the right vibeand the right conversation.
Then you move into other piecesof that, then the situation
awareness, obviouslyhousekeeping at the end and that
.
So that Friday ritual is greatbecause things are flushing out
in that Friday.
Then Monday morning I sit withmy leaders and we say, okay,
(17:47):
here's the three objectives thatwe need to do for the week.
Those are what important to me.
Do we understand each other?
Do you see things the way thatI see them?
Do you understand thepriorities?
Do you understand the how andthe why?
Interesting.
Josh LeQuire (18:00):
So it sounds like, david, you've got an opening
and a closing almost to a weekright.
You've got your opening ritualson Monday, your closing rituals
on Friday.
Friday is celebrating success.
Monday is all right, let's getfocused.
David Kestenberg (18:12):
And it's a lot more than that, because Friday
you go to the team meeting, butThursday you're doing the
dashboards.
You're doing the dashboardsbecause there's also going to be
an exec meeting on Friday, notjust a team meeting on Friday.
So it's moving in a certain way, but I want to put the
spotlight on full team, not townhall, not something that
(18:35):
everybody needs to dress up,something that everybody's
coming with their lives,something that everybody's happy
and smiling to see each other,that type of meeting.
And then Monday it's a lot morebrief.
It could be a call, it could bean email, it could be guys,
very clear, regular week, threeobjectives.
All right, kill it, let me know, control your sector.
If you have problems, let meknow, I'm here, that's it, you
(18:56):
know.
It could be.
It could be five minutes on onmonday, but it's important to
invest the time on friday withthe team.
Let them go to the weekendfeeling appreciated, but for
real, by their teammates, not bysome dude, some suit like by
the teammate.
Josh LeQuire (19:17):
Feeling seen is really really important to want
to come back on Monday.
The theme of collaboration hereis phenomenal.
I share an opinion here withyou that I'm sure you have, that
when you foster that level ofrecognition among teammates,
that positive reinforcement loop, just compounds and compounds,
and compounds.
It brings people closertogether.
It helps to achieve resultsvery effectively.
(19:38):
What are some other ways tofoster that kind of
collaboration day to day, notjust on Fridays, with
recognizing a team member?
David Kestenberg (19:47):
You know, I think that it's very important
to bring yourself and your wholeself into the story, and
sometimes it's difficult.
Sometimes people are more.
You know, not everybody is anextrovert, introvert.
I don't want to talk about mydad, my kids, my dad.
(20:08):
Some people are verycomfortable doing that.
Everybody has something thatthey really like to talk about
and once we make them feelcomfortable, they will.
And it can be.
You know, we just had Passovera week ago.
Talk about freedom from aJewish perspective.
It can be a part of a meetingbecause it's, you know, it's
inspiring.
And then, you know, because ITis super diverse, you get to
(20:33):
have all you know, the indianculture coming in with the wally
and with cricket, and obviously, people that actually
understand soccer, not likeamericans.
And so if there was a gameyesterday, there is not a
problem to open a meeting withtop of mind have.
Have you seen Barca yesterday?
Yes, no, was it cool?
(20:54):
Move on.
And when you bring yourself andit's, you lower the walls,
we're already connected onsomething.
I know that he's a cow guybecause he keep wearing all
those brands.
Great, now we have something tojudge on as people and not, as
you know, bricks Like yeah, I'mba on this project and this is
(21:15):
all the things that you willhear from me.
Otherwise I'm a bot, you know.
So, humanizing the individualopening the door, and it's
dangerous, I have to say.
You know, hl don't like it.
Josh LeQuire (21:26):
They are not sometimes people bring a little
too much through the door well,yes, no, no.
David Kestenberg (21:31):
You know we need to have boundaries in the
way that we do that.
But when I started those Fridaycalls and then COVID hits, we
had to talk about difficultthings.
People were afraid.
People had both financialcrisis and health crisis and
isolation.
Now everybody wants to workfrom home.
But you know, five years ago,definitely for people that were
(21:54):
at that time 22, 24, that wasit's big or people that got
locked in the house, you know,after working in the office for
15 years, opening the door totalk about those challenges,
yeah, you're kind of walkingthis HR line that they might say
, hey, you are, you can be aliability here and I'm like, as
(22:14):
long as it's all in positivenote, it will increase
productivity.
Josh Matthews (22:18):
The thing that I keep hearing is accountability
and zero ambiguity, like thosetwo things combined with
vulnerability.
I'd say those three things seemto be echoing through you, and
I don't think I'm wrong here.
I think this is what you'resaying.
So when we look at Thursday,it's your dashboards, friday,
(22:39):
it's your big meeting, it's yourbig vibe meeting, right, and
it's a hoorah.
But at the end of the day, youcan't have ambiguity in these
situations and it's reallyimpossible to scale without
trust, and I had the fortunateopportunity to spend a couple
hours in the last month or sochatting with someone who
(23:00):
reported directly to you Verybright, very smart.
Are we dropping?
David Kestenberg (23:04):
names.
Josh Matthews (23:07):
No, we're not going to drop names on the show.
David Kestenberg (23:09):
We'll see, he's a call guy he's a car slash
boat guy.
Yes, yeah.
Josh Matthews (23:15):
Yeah, axar, highly intelligent, very bright,
and it made so much sense to mewhen we, when you and I talked
and and then, after alreadyhaving spoken and spent some
time with Axar, it's like, well,yeah, if you've got people like
Axar on your team, of courseyou can feel confident in
delegating, but you're the onewho has to pick those
(23:39):
lieutenants under you thosedirectors?
What do you do, like, aside fromlike the tech check and the
vibe check?
I get that because you and Ithink we're very similar
personality profiles.
You do a different profilesystem than I do, but I
correlated it and we'repractically the same.
We're very different peoplewith very different experiences,
but we kind of approach theworld, I think, similarly.
(23:59):
We see the same information, wemake decisions kind of based on
the same things.
When you personally have tobuild your team of lieutenants
or your team of directors andmanagers under you, that's
different than scaling 70 peoplein three months right, I need
three to six people and I needthem very quickly.
I need three to six people andI need them very quickly.
I'm just curious what do you dofirst?
(24:20):
Do you check your network?
You call your favoriterecruiter, you post an ad on
LinkedIn?
No, no, only network Onlynetwork.
David Kestenberg (24:28):
We're old enough to be able to say, for
that intimate role that isreporting directly to me and
need to be one of four, maximumfive people, then it's most
likely people that I alreadyknow.
It can be that they weremanagers before and now I'm
(24:49):
ready for them to be directors.
So you know, when I moved fromdifferent places, people that
were maybe a little bit lowermoved up and now reporting
directly to me, but it's usuallywithin that clan, within that
group of people that I know.
But I want to touch on, well,two things.
One, when you were talking aboutthat vulnerability element and
(25:10):
lack of ambiguity Right, Idisagree as strongly as I can
about the ambiguity.
You can be extremely clearabout your ambiguity, extremely
clear.
You can come to your team andsay here, guys, here's the
situation.
We don't know if the client isgoing to do A or B and we will
not know.
In the next 27 days we willneed to operate without knowing
(25:33):
that situation and maybe it'sgoing to be A, b or C, but we
will not know.
And I need you to be agile andvigilant and all those amazing
adjectives, but it's stillambiguity.
But it's clear that it's that.
Josh Matthews (25:48):
That's still zero ambiguity as far as I'm
concerned.
I mean, these guys are running200 miles per hour around the
track.
They've got a plan A, plan B,plan C, like you've got to plan
for alternatives.
So that's fair enough.
But I think when we're talkingto our team members and we're
trying to understand what'sgoing on with them, the clients
can be ambiguous.
Right, there's 10 other peopleover in that firm.
(26:10):
They're all meeting, they'retrying to come up with some
ideas, they're waiting forinformation from us.
Then it's a back and forth loopand we're going to get it.
But when we're talking to thosemanagers under us, when we're
talking to those directors, Ourcore value is not changing.
David Kestenberg (26:24):
We will always do the best we can the fastest
we can at the lowest budget thatwe can.
They understand that.
Josh Matthews (26:30):
But there's still zero ambiguity.
It's like don't feed mebullshit, don't feed me bullshit
, Don't tell me you don't know.
If it's something that youcould find out, go find it out.
It's not like don't find outjust because you don't feel like
finding it out.
David Kestenberg (26:46):
Go find it out .
You know what.
Let's connect that to how Ipick my people.
So part of how I pick my peoplethat's the part one is that.
Part two is I need to be ableto tell them that sounds like a
you problem.
Because that sounds like a youproblem is like I trust you, I
believe in you, control yoursector, solve it.
And if you don't need that, if,if you cannot raise a flare, I
will be there before the flareis going down.
You know that's.
(27:07):
But someone that cannot acceptit sounds like a you problem and
and will freak out, probablycannot be in the immediate
circle.
So there's a couple of filterslike that and in my head I have,
you know, a color system andobviously green is the account
management and the vendormanagement, the money side, the
(27:31):
budget of labor, budget oflicenses, budget, that.
So there's a green guy and he'sgoing to do that.
There's always in the fivepeople team.
There's always going to be thatguy.
And then there's going to be adev guy.
It doesn't need to be a VP ofengineering, it needs to be
someone that can take zero toone, that can drive the team
into something.
That was not there yesterdayand now it's there, that guy.
(27:51):
And then there needs to besomeone that can speak with
everybody, that can go to theproduct team, that can go to
client side and they can go tothe dev and be kind to all of
them, understand, speak all thelanguages and be able to do that
the Minister of Foreign Affairsoffice.
So when I'm sitting and I'mmaking my Israeli salad to my
(28:13):
media team and we're sitting andeating and talking, you can
look around the table and youwill see that they can all bond,
but they are extremelydifferent because they have
their sectors.
There's overlapping between thesectors.
Obviously, the dev guy needs tobe on the same page with the
money guy and the money guyneeds to be on the same page
with the guy that makes thepromises, the solution guy.
But they are very, verydifferent and for me it's like
(28:36):
there are four or five seatsthat we need to fill and if we
do that, under them they willknow how to build those
lieutenants and below thelieutenants, and that they will
know how to scale those teams,because the machine has the
logistic element, the core, youknow, the fighting force and
then the rest of the fluff thatwe need to have, so it's's.
Josh LeQuire (28:57):
I hope it makes sense that it doesn't well, I
think, david, what I'm hearingis like you, you seem.
I don't know if this is innateor you've developed this through
experience working, you know,kind of in the civilian sector,
or if this came through some ofyour military training.
David Kestenberg (29:10):
It's more of a ceo behavior than uh, yeah, uh
than a lieutenant or I happen tobe a major, but like it's more
of a CEO perspective, I need theCFO to deal with the money.
It happens to be a manager thatjust deal with the 50 people
budget.
Josh LeQuire (29:25):
This is great because, david, you're right.
I think what it sounds likeyou're kind of leaning into is
what kind of roles do I need,who's the best fit for that role
, and how can we, day by day,develop people in those roles
and develop people to rely oneach other for their individual,
unique talents across the team?
Josh Matthews (29:43):
Ladies and gentlemen, this has been
Salesforce Hiring Edge withDavid Kestenberg, and if you'd
like to connect with David, youshould.
He's on LinkedIn, kestenberg,k-e-s-t-e-n and it'll come right
up.
That's B-E-R-G.
By the way, david, thank you somuch for being on our program
today.
Happy to be here and, by theway, you're welcome back.
In fact, I think you're comingback for another episode.
David Kestenberg (30:05):
I hope so, if you'll help me.
Josh Matthews (30:07):
Absolutely.
We'd love to have you on.
Thanks so much, david and Josh.
Great questions today.
Thanks everybody.
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