introducing the diSaaSter recovery podcast

we’re on a mission —

to simplify startup life for the doers.

startup addicts & SaaSholes in sales, marketing, product and more face trials and tribulations, chaos and confusion, and ups and downs that  corporate counterparts may never understand (or know). 

their stories of hope, failure, frustration and more will leave you saying, "what a disaaster!"

this show features their stories and your way forward.

welcome to diSaaSter recovery —

the podcast that presents a practical portrayal of the pandemonium and predicaments that come with working in SaaS companies. 

join us as we converse with professionals from diverse roles and functions in startup SaaS companies and hear their horror stories and invaluable lessons learned.

unlike other SaaS podcasts —

that concentrate on success stories and best practices, our show centers on the unpleasant realities of working in the industry. 

from missed milestones to malfunctioning features, from bungled launches to bitter customer complaints, we delve into the challenges and chaos that SaaS companies confront daily.

our interviews assist listeners —

in recognizing the warning signs of a company on the road to disaster and provide illuminating insights on the steps they can take to recover. 

we believe that by sharing these experiences and lessons learned, we can help others avoid making the same slip-ups and build more resilient and successful companies.

join us —

and step into the world of startup SaaS companies with usand discover the diSaaSter recovery stories that are often left untold. 

whether you're an entrepreneur, a software developer, a marketer, or just someone intrigued by the SaaS industry, this podcast is for you.

Episode Transcript

josh (00:07):
Welcome to the Disaster Recovery Podcast.
I'm your host, josh Santow, andthis is the show where we
reveal the untold horror storiesand hard-learned lessons of
software as a service start-uplife as told by the sassholes
who lived through it.
Their stories about themanagers, departments and
companies they worked for willleave you thinking what a
disaster.
Our mission is to help youbring order and sanity to the

(00:30):
chaos you will undoubtedlyencounter in your own adventures
in sass.
There's stories andconversations with our guests
who have been there and donethat in all aspects of sass,
from sales, marketing, productand more.
You'll get the tools andinsights you need to recover
from disaster.
Welcome to episode 0 of theDisaster Recovery Podcast.

(01:02):
This is just a preview to letyou know what you could expect
when you listen to the DisasterRecovery Podcast.
We're going to be talking aboutthe who, what, where, when and
why of the show.
The Disaster Recovery Podcastis for sass and start-up
professionals across sales,marketing, product and more, who
we lovingly refer to assassholes.

(01:23):
It's where they share horrorstories and hard-learn lessons
from their time in sass.
It's all hosted by me and myname is Josh Santo.
I spent nearly my entire15-plus year career in sass and
I pivoted halfway through fromcorporate life to start-up life.
I've worked in pre-salesimplementation, customer success

(01:44):
and support, product marketingand product strategy, as well as
other roles, because at astart-up you wear multiple hats
at any given time.
I've seen a lot, I've done alot, I've learned a lot, and
I've done all of that the hardway.
So each episode we're going tobring on a guest and we're going
to introduce our guest, providesome background and really dig

(02:06):
into their expertise, and thenwe're going to hear from them a
horror story and a hard-learnlesson.
Then we'll find out how they'veapplied that lesson to their
career and situations goingforward.
Episodes will be distributedweekly after we officially
launch.
This, again is just a preview,so it's not the official launch.

(02:27):
Now, why are we doing this?
Well, we're on a mission.
We want to simplify start-uplife for the doers.
We believe that building greatcompanies requires
accountability.
Total accountability withincompanies is not possible
without an informed workforce.
And to help you avoid some ofthe pains of experience, we're

(02:50):
bringing you the real life,untold and unfiltered
experiences of your peers.
By sharing and relating to oneanother, we can minimize the
hard times and use newfoundperspectives to hold people
accountable.
So, since each episode is goingto be centered around a story,
a horror story I thought I wouldshare.
What a mind, a very hard-learnlesson that I learned, and

(03:13):
pretty recently.
So I worked at a major techcompany before getting into the
start-up life and I startedtaking phone calls for support,
worked in Tier 1, customersupport.
Tier 2 became what was known asa senior specialist at this
organization, which isessentially a type of subject
matter coach.
Throughout that process Ilearned the value of positioning

(03:37):
, which ultimately set me up formy product marketing roles,
because it's very much an art togently and positively position
bad news to people you can'thelp, who are mad about the
product that your company sold.
And I worked hard.
I learned a lot.
I was taking hard phone calls Iwas supporting, eventually

(04:02):
negotiating support processeswith internal stakeholders I
think about that term that Ijust used, internal stakeholders
God, that sounds so corporate.
Anyway, for years in a rowactually, my yearly performance
reviews were the highest on theteam and in the department,
which was exceeds expectation.

(04:24):
So all the way across, exceed,exceed, exceed.
Essentially, my management wastelling me we don't have any
other feedback for you exceptgood job.
And I got to a point where Ifelt stuck, I felt underpaid, I
felt underutilized and I was ata crossroads.
I could either move into callcenter management or I could try

(04:45):
to break through the politicalhierarchy of the company and
ultimately make a move fromTexas to California.
That was until a future friendit wasn't a friend at the time,
it was complete stranger.
At the time reached out to acurrent coworker looking for
help.
He told her that he neededstrong recommendations for a

(05:06):
startup that he worked at, andso she introduced us, and this
is what ultimately kicked off mystartup experience.
From off the cuff interviews,chaotic onboarding and a trip to
Puerto Vallarta, mexico, markedthe beginning of my startup
life.
Working out of a small, openfive person co-working space in
downtown Austin, and because wesat so close to each other, I

(05:30):
often heard sales calls.
Now, my background, my personalbackground, is in performance.
I used to do a ton of theater.
I did a lot of improv,particularly in the Austin area,
and when I was in that office Igot to see sales calls and
demos and when I saw them Ireally thought of them as mini

(05:53):
performances and I knew that Icould do that too.
So I busted my ass to onceagain exceed expectations at my
job and at the same time startedpushing out, pushing on the
director of solutions consultingto consider me for the opening
that he had on his team.
But he wasn't convinced atfirst, probably because I didn't

(06:13):
have any sales or pre-salesexperience.
And solutions consulting can getpretty technical.
You have to know who thesolution benefits, how, what the
possible return on investmentcould be.
You have to overcome objections, you have to deal with
detractors, you have to tailorthe message in the moment to the

(06:36):
audience and a lot of times youhave to make all the materials
up that you need in order to getthe job done, to get the sale
to happen.
And so he decided that thiswasn't the right role for me.
But after some time it's inpersistence, and in particular,
he saw me challengingrespectfully of course our

(06:57):
leadership on a few differenttopics during an all hands
meeting in front of the company,and when he saw that he had
what he needed, he ultimatelyoffered me the job, and that
changed my life, that changed mycareer, and I'm very grateful
for the opportunity and thechance that was taken on me.

(07:18):
So if this was a movie this iswhere a montage would start to
play.
I'd be going on site tocustomers not knowing what the
hell I was doing, but deliveringsolid, engaging demos.
We won a lot of deals, we losta lot of deals and throughout it
all I was having a blast.
And this went on for a fewyears.
But I'm a millennial and I gotthat millennial itch, the one

(07:43):
where it's time to find a newrole because you're not really
sure that you want to do thisexact role for the rest of your
life.
Plus, we had just hired a newCRO and I knew pretty quickly
that this was an individual Idid not want to work with.
I did not trust and, as luck orfate would have it, our

(08:03):
short-term product marketerdecided to leave and he always
appreciated the conversations heand I had together talked very
much about thought, leadershipand how to define the category,
the market category that we werein, because it was an
up-and-coming market category,and he said that he thought I'd
be pretty good at productmarketing and if I was
interested, he'd put in a goodword.

(08:24):
So that's how I became aproduct marketer and once again,
I had no idea what the hell Iwas doing.
So I tried to focus first onmessaging and that was really an
effort, trying to get the wholecompany to not only think about
our product and our market aspecific way, but to speak about
it a specific way as well.
I drove and created newcompetitive intelligence

(08:45):
programs.
I instituted win-loss analysisprograms, which were one of my
most favorite activities becauseI loved just having the
opportunity to really dig intothe why of a decision.
Why did they choose oursoftware?
Why did they not choose oursoftware?
It'd be very critical andreally understand so I can take

(09:06):
that and feed it back to theproduct team, to the sales team,
to the marketing team and tothe company so that we could
continue to improve, because ata startup it was all about
iteration.
I launched products features,launched an industry specific
podcast that made numerous top10 listicles for industry
content, I hosted webinars.

(09:28):
I led session at events in more, and this went on for years.
And as I continued to getpromoted all the way up to
director of product marketingand then director of product
strategy, I had a toughrealization.
I was not happy.
I was doing things that I likedto do, not really loved, but I

(09:52):
liked it.
But I just I wasn't happy.
So I took some time to reflecton why and talk with close
colleagues and my wife, andprobably bitched way too much
about life at this particularcompany, and that's when I
realized what had happened.
I no longer had my life.

(10:13):
I no longer felt in control ofmy time or energy or passions.
I had spent years giving my allto a company, sacrificing
friendships and hobbies thatindividuals need in order to be
fulfilled individuals.
That was my disaster and thatis what I'm on the road to

(10:34):
recovery from.
I let the allure of the startupworld, the promise of riches,
the corny missions, strategiesand statements, the promotions,
consume me.
I could count on one hand, thatpeople I'd call friends, I'd
gained like 50 pounds, I'd quitall of my hobbies.

(10:57):
So I quit, and while there werea lot more reasons behind that
decision, it was one of thegreatest influences on my
decision.
I quit and I started a journeyto take back what I willingly
but unintentionally gave up,which was my time, my happiness,
my life and one thought thatstruck me after leaving, after

(11:22):
going through some of the stagesof grief, after reflection,
what I was left with was thisidea that, had I known better, I
could have done better, andthat's what led me to this
podcast.
Disaster recovery podcast is forthose sassholes like me, those
passionate, committed, skilledpeople who could use a sanity

(11:45):
check, who could use reassurance, who could use some guidance
without the buzzwordy bullshitthat gets tossed around in the
workplace.
I want to know better so that Ican do better and be better next
time.
I want to be able toeffectively push back, when I
need to, on unaligned,ridiculous decisions being made
by people who just happen tohave a specific title and if

(12:09):
you're listening to this, I betyou do too.
So if you want to learn moreabout my story and the stories
of others just like yourselfacross sales product marketing,
if you want to cut through allthe BS that gets thrown out in
VC-backed startups lots ofbuzzwords out there can't wait
to talk about radical candor.

(12:30):
If that's something thatresonates with you, then this
show will resonate with you.
Until then, keep an eye out, oran ear out, for the next
episode and feel free to checkout our website,
wwwdisasterrecoverycom.
Keep in mind that there'sanother A in disaster, because

(12:52):
it's a play on SaaS.
I'm sure you got that, though.
Okay, thanks.