November 17, 2024 • 32 mins
In this episode of On Boards, Chris Cuddy, a seasoned executive and board leader with over 25 years of experience growing technology-enabled companies in both the private and public sectors shares invaluable insights into the evolution of a company’s board as it progresses through different growth stages. He discusses how the board’s role shifts over time from hands-on support to formal governance.
His unique perspective is informed by his extensive career, including key roles in companies like Cheapflights, Engage, and ezCater, as well as his background in consulting, investment, and board leadership.
Key Topics Discussed:
- Stages of Board Evolution in Startups
- Seed Stage: Founders are often the primary board members, with activities blurred between governance and management. Chris recalls the “early days” of ezCater, likening the stage to “two founders and a PowerPoint.”
- Startup Stage: Boards begin to focus on defining product-market fit and may introduce angel investors. Chris describes his hands-on involvement with ezCater at this stage, from customer calls to financial planning.
- Growth Stage: The board’s role formalizes with the introduction of venture capital. The addition of independent board members and committees becomes essential in order to scale. Chris shares how ezCater’s board evolved to support rapid expansion across the U.S.
- Maturity Stage: The board is now primarily focused on governance, with a clear distinction between board and management roles. Chris reflects on how the board transitions into “maintenance mode.”
- Renewal or Decline: Boards help strategize paths to either reinvigorate or prepare for acquisition. Chris recounts his experience with Engage, navigating challenges during the tech bubble burst.
- Key Traits of a Functional Board
- Selecting board members with domain expertise, cultural fit, and a shared commitment to supporting the company.
- Chris discusses the importance of a highly functional board in advancing a company’s mission and creating stability.
- The Role of the Board Chair
- Chris highlights the importance of the board chair as a bridge between the founders and board members, ensuring transparent communication and balanced input.
- He shares insights on the unusual longevity of his role as ezCater’s board chair, attributing it to his ability to adapt as the board and company evolved.
- Unique Challenges and Responsibilities in Early-Stage Boards
- Chris describes the blurred line between governance and management in the initial stages, emphasizing that board members may often act as extensions of the executive team, especially in strategic, operational, and fundraising efforts.
- Building the Board with Intentionality
- Chris emphasizes t
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:05):
Hello, and welcome to On Boards, a deepdive at what drives business success.
I'm Joe Ayoub, and I'm herewith my co-host, Raza Shaikh.
Twice a month, On Boards is the place tolearn about one of the most critically
important aspects of any company ororganization; its board of directors
or advisors, with a focus on theimportant issues that are facing boards,
(00:28):
company leadership, and stakeholders.
Joe and I speak with a wide range ofguests and talk about what makes a board
successful or unsuccessful, what it meansto be an effective board member, and
how to make your board one of the mostvaluable assets of your organization.
Before we introduce our guest today,we want to thank the law firm of Nutter
(00:52):
McClennen & Fish who sponsored our OnBoard Summit recently in their beautiful
conference center in the Boston Seaport.
They've been incrediblepartners with us in every way.
We appreciate all they'vedone to support this podcast.
Our guest today is Chris Cuddy.
Chris has spent over 25 yearsbuilding and growing private and
(01:13):
public technology enabled companieswith an international focus.
He is board chair of ezCater, thenumber one food tech platform for
workplaces in the United States.
Chris has also served as CEO ofCheapFlights, an international travel
search engine acquired by PricelineKayak, CEO of Engage, a pioneering
(01:38):
online advertising network, now NASDAQlisted, acquired by JDA Software, and
Chief Commercial Officer at FarePortal,a leading online flight travel agency.
He has also held senior roles atCMGI, Computer Sciences Corporation,
(01:58):
Lightbridge and Goldman Sachs.
Chris was an early team member at BlueStreet Technology and Mecca Software.
He has served on the boards of public,private, and non-profit organizations,
and is an active angel investor andsupporter of early-stage companies.
(02:20):
Welcome, Chris.
Thanks so much for joiningus today on On Boards.
Well, thank you, Joeand Raza, for having me.
I admire the legacy of board membersthat you're compiling in these podcasts.
Thanks.
Chris, let's start with your background.
Can you talk about your journeyfrom Goldman Sachs to being
(02:43):
the CEO of Cheapflights?
Yes, Raza.
Well, it's a long and windingjourney, and it's really included
three different perspectives thathave shaped how I view boards.
First, I've been in the boardroom as amanagement consultant to executive teams
of large public companies for 10 yearswhen I worked at Index, and this was with
(03:05):
large public organizations; the WashingtonPost, Nielsen Media, Duke Power.
I've also been in the boardroom asan executive board member, and that
was as the CEO of public and privatetechnology companies in the US and
Europe, including Engage, which wasthe online advertising pioneer, and
Cheapflights, the online travel pioneer.
(03:25):
I've also been in the boardroomrepresenting investors when I worked
at CMGI, which was the internetincubator, and as an independent
investor with companies includingezCater, which is the only nationwide
corporate catering marketplace.
And this has been across public, private,for profit, charitable, and across
(03:45):
all stages of a company's life cycle.
That is a tremendous breadthof background, Chris.
Maybe talk a little bit moreabout the early part of ezCater.
Specifically, kind of the story of howLaunchpad, a group that you and I both
are a member of as investors, invested inezCater, and how did that journey start?
(04:10):
Yes.
Well, as you know in 2012, ezCaterwas a five-year-old company with some
incredible, really extraordinaryco-founders, Stefania Mallett and Briscoe
Rodgers, who had spent five years workingat the kitchen table on a great idea
(04:32):
to launch an online marketplace forcorporate catering and a marketplace,
you may know in many other forms, iswhen you bring together both customers
and suppliers on the same platform.
Actually, ezCater was calling itselfthe Expedia for corporate catering
just so people could understand.
And after five years, they werelooking to raise capital beyond the
(04:54):
friends-and-family rounds that they haddone and they had a lot of eagerness
to learn what they didn't know, a lotof eagerness to add some marketplace
knowledge to the board, and the board atthat time was Stefania and Briscoe and
another early independent board member,Mike Masterson, who was very experienced
in early stage CEOs in pharma and biotech.
(05:18):
Chris, was that the time when youactually joined the board post-investment,
or did you join earlier than that?
So, when ezCater came to Launchpad, theywere looking for their first organized
angel group funding round, and they didcome to the group early in their process,
(05:39):
and we launched some diligence on thecompany and spent weeks looking over
their vision, looking over their books.
Originally, Launchpad declined toinvest because the business plan was not
yet structured around the key driversfor an online marketplace, but to the
co-founder's credit, they really tookthe feedback, modified their plan, and
(06:01):
the results of that process were thatLaunchpad led the series, A&A, when Rick
Fedorowich joined as a board observerfrom Launchpad and then I joined as
the board chair, and that was a realmilestone for the company because it
was their first round of professionalfunding and the board changed composition.
This was going from a board of twofounders and one independent to now
(06:23):
a board that had two founders, twoindependents and an independent observer.
Chris, that really came about because,in part, your operator experience
in actually building marketplacesbefore, as you mentioned, for example,
the cheapflights.com was also basedon a marketplace model and that's
(06:46):
what led you to joining the board,bringing your experience to the table.
That's right.
And I think, in my experience, thisis indicative of this early stage
of a startup's life in which thedistinction between a board member and
an executive board member, a founder,can actually be very blurred, and I
(07:06):
think oftentimes the board members becomean extension of the executive team.
There are many things that in thatearly stage that I was involved in.
It was everything from interviewingteam members to working on the financial
forecasts, to working on what themodel actually was that was driving the
company, and that all happened, I think,at a frequency that was quite intense.
(07:31):
We had board meetings once a monthfor several years, but probably
more than half of the time I spentwith the board was unscheduled and
was outside of the board meetings.
So, they were ad hoc as they came up,opportunities, problems, questions,
that took the natural rhythm ofwhatever the co-founders were facing.
Yeah, it's a great point.
We talk a lot about boards and whatboard responsibilities are, and one
(07:55):
of the things that we talk about, andpretty much all our guests talk about,
is the distinction between governanceand management, but as you pointed out,
that gets blurred in some instances.
So, it would be great to spend a fewminutes, given your pretty unusual
perspective, deep and broad, infor-profit, investment-backed boards to
(08:19):
go through the stages of evolution ofa board, because it really is different
than a lot of other types of for profitand certainly non-profit companies,
so let's start with a little bitabout your perspective on watching and
observing the evolution of these boards.
(08:40):
Yes.
I think in my experience, we can usekind of the classic five stages of
a company's development, and you canmap that with what the focus of the
board is in each one of those stages.
If we go through them on the toplevel, the early seed stage for
ezCater was when they were foundersin the kitchen table, and at that
(09:01):
stage, they're basically self-funding.
They're trying to get clarity on the ideaand they may or may not have incorporated,
they may or may not have a board.
And if they do have a board, it's usuallyheavy founder based, and as I said,
even in this phase, it's very hard todistinguish board member activities
from founder activities sometimes.
But the goal there is to basicallyget the idea crystallized so they can
(09:26):
approach potential funding later on.
Yeah, I love the way you put it; ideastage, two founders and a PowerPoint.
So, it is really down to the mostbasic beginning, and then it's going
to take a lot of time, effort, luck,perseverance, super talent to even
(09:46):
get to the startup stage, whichI think is the next stage, right?
That's right.
After the seed and developmentstage, starting with two founders
and a PowerPoint, what is thenext stage that you've observed in
for-profit, investment-backed boards?
Yeah.
So, hopefully the seed and developmentstage can get followed by an actual
(10:09):
startup stage, because they'vecrystallized what their idea is,
they've got a business plan or at leastthe first version of that, and they
really want to go to a stage wherethey can focus on clarifying the early
product market fit where they canmake sure that they have a business
(10:30):
that they could pitch to investors.
At that stage, they might be lookingto raise their first organized angel
round, which is where we met ezCater.
And what does it take for them at thisstage to validate their business model?
What do they have to show the investorsand maybe their board in order to
(10:51):
actually succeed at that stage?
Their proof points that are super helpfulat this stage are anything that they
can show that convinces an investorthat they've got early product market
fit and that they've got a repeatablemodel that's actually going to scale.
So, this means that they've got customerfeedback, this means that they've got
(11:13):
supplier feedback, and they can showthat these are not just one offs,
they can show that they've actuallytapped into a vein of need and they're
uniquely providing some value for that.
And the board's role is still kind ofblurred between governance and management?
I mean, you're still workingwith management to get
through the startup stage.
(11:34):
Is that right?
Yes.
And even to the point where in this stageI've been doing customer calls, going door
to door with a sales rep to really try tosense if the model is getting traction.
So, it can be wearing many hats.
It can be actually workingon financial forecasts.
It can be actually coaching the CEO.
(11:56):
Many times when you've got co-founders,they have worked together before and
many times they have not, and very oftenthe roles that they're in are roles that
they're taking for the first time, andbeing the first time CEO, they could
really use the guidance of someone who'sbeen in that role before, and that's
(12:17):
often one of the most helpful things thatyou're doing because it's really a grab
bag of whatever is on the founder's mindand whatever hurdles they're coming across
at any given day for you to be able tostep in and either give them guidance,
give them a hand or direct them to someresources that you know that can help.
So, it's really all hands on deckas far as the board is concerned and
(12:38):
helping them validate the model so theycan get to the growth stage, which is
the next stage, is that about right?
That's right.
And I would say that between the firsttwo stages, the seed and the startup,
it's still a very fragile environment,and one of the things as a board
member that I think it's importantto remember is that investors, board
members are attracted to a company inthese first two stages, in large part,
(13:01):
because of the founders themselves.
They don't yet have cash flow.
They don't yet have an idea thathas been proven beyond a doubt.
You're really drawn to the individualswho are on that founding team, and
it's very important to remember thatand to listen to them because that's
what attracted you in the first place.
So, I think I consider myself a fastfollower and maybe anticipating what's
(13:23):
going on, but that's a differencebetween putting a hand on the steering
wheel, and I think if you get to thatsituation, then you have to step back
and question whether this is the rightopportunity for you as a board member.
Yeah, that is a great point, thatyou really still have to keep the
focus on the fact that you're therebecause of the founder or founders,
(13:45):
and that listening to them isimportant if you're going to help them.
Yes.
Yeah.
So, the next stage is the growth stage.
What does that entail?
What does it look like, and what's themoney aspect that have you now grown?
Is it out of angel into VC?
Is it something else?
Yes.
That the characteristics of thegrowth stage are when the founders
(14:08):
and the founding team has some earlycustomer and financial success with
some increased predictability now andthey've really proven that they have
the potential to accelerate growth.
So, at this stage, they're lookingto ramp up operations, and that very
often requires additional funding.
I'll continue on the ezCater example.
(14:30):
They had been chasing a huge opportunityin the first two stages of their
growth, but they didn't feel like theywere moving fast enough, even though
as the founder says their growthrates had growth rates at that time.
They didn't feel like they weredoing everything they could.
They thought it would be a very longjourney to actually go state by state
and caterer by caterer on the angel groupfunding levels that they've raised so far.
(14:54):
So, at that point, the board wasasking, how can they accelerate growth?
What would be the fastest way tooffer catering in all 50 states, and
what if capital wasn't a constraint?
And the answer that they reached is,I think, very typical for the growth
stage, which is that the ambition andthe timeframes that they were talking
about required venture capital, andthat was a big conversation because
(15:18):
the founders had prided themselvesup to this point on frugality.
So, the board went through somereal soul searching about would
this change the DNA of the company?
Would we lose control?
Or can we take on morepartners and satisfy everyone?
So, I think that's a very emblematic,dynamic of this stage, and for ezCater
(15:40):
at least, the board did approvethis ambitious path that was venture
funding enabled, and basically kickedoff a process of reaching out to VCs,
which winds up being a heavy liftfor some co-founders who are managing
the business in the daytime and atnight, they're getting introduced to
VCs, they're exploring them, they'rereaching out, interviewing, and
(16:03):
the whole process of that entails.
Is the board composition stillpretty similar to the way
it was in the startup stage?
It hasn't really shifted until theVCs come on or new investors come on.
Is that right?
Or is it already changing?
That's my experience.
I think the board at thisstage was co-founders when
(16:24):
they were in the seed stage.
They maybe brought on some angelswhen they were in the startup
stage, but it's still a board thatis maybe four or five people and
you're still wearing multiple hats.
I think the growth stage is really whenyou're injecting a degree of formality.
Now, this is when you need toformalize an audit committee.
If you haven't had a comp committeealready, you need to put that in place.
(16:47):
Because the venture model has a rhythmto it, and it has some standards to
it, and it's going to require reportinglevels that you may be as a co-founder
haven't been delivering to your investorsas frequently with the same rigor.
From the growth stage to the nextstage which you call maturity, what is
(17:07):
happening, and what would define whatgets you to the so-called mature stage?
Yeah.
In the growth stage, one of the things Ithink to remember every time you've added
people to the board is that these arelife changing decisions for the founders
and these are multi-year relationshipsthat you're reaching out to create.
(17:28):
Before you leave the growth stage,it's very important to build the board
intentionally with that long-term view andreally make sure that you're building a
board where people have not only a domainexperience that they can bring, not only a
cultural fit, but also people who have thesame intention, and that will very much
help you to get through the growth phase.
(17:49):
By the time you get to maturity, thisis for most businesses many, many
years out, and this is when you've gotpredictable and stable revenue and a
strong brand, and at this point, theboard structure should be humming along
and this is really all about execution.
Is this board at maturity now, morereflective of what we think of as the
(18:13):
kind of board roles that are most common?
In other words, you're not sittingdown late at night with the
founders anymore, or maybe you are.
Is it more governance and lessday-to-day kind of work that is very
much part of what management is doing.
Yes, maturity level for companies iswhen the board gets into the rhythm,
(18:36):
they get into the cadence, you havecommittees, you've got responsibilities,
you've got succession planning going on.
So, the structure of the companynow is well understood, and as
far as the board's going, it feelsmore like a maintenance mode than a
putting out fires and running aroundsupporting every founder's activity.
(18:58):
Are the founders still on the board,number one, and number two, are you
able to look around at this point forindependents who are not necessarily
investors that can come in because theyhave something in their background;
it may be domain experience, maybe operational, it may be something
else that is critical to the successof this company at a mature stage?
(19:22):
Yes.
especially from mature companies thathave gone to the public markets at
this stage, you're definitely goingto be looking at a full-fledged board.
You're going to have independents inthe appropriate ratios and this is
a real now stable, kind of reliablecomponent of the organization that
is distinct from the management team.
(19:43):
I think it's at this mature stagewhere for the first time you see the
clear delineation of those two roles.
And the last stage that you have, Ilove the way it is, it says renewal
decline, which makes me think you cango either way, and it also makes me
think that these five stages is partof a cycle that can now repeat itself.
(20:06):
Because if there's a decline, then I wouldguess there are things you do to get back
to growth or get back to some other stage.
Can you just talk a bit once there'smaturity, how do you keep it going?
How do you either address the declineor make sure that you're renewing it,
energizing it, making sure it's wellfunded, well governed, et cetera.
(20:28):
They fall into this renewal and decline.
For some, they're able to rejuvenatethemselves and for some, they're not.
I can actually give a story of onethat that was not able to do it.
This is a company that was very highgrowth that had intense competition.
This company was called Engage.
It was a public company on the NASDAQ,and it was one of the high flying
(20:49):
pioneers of the online advertising space.
They had an incredible product wherethey could do anonymous profiling.
They could serve you an ad specificallytargeted to you without having any
personally identifiable information.
It was great and things weregoing well when they ran into
the Internet bubble bursting.
(21:10):
So, this was not of their ownmaking as much as they got caught
up in really economic headwindsthat turned into a downturn.
So, the board was really faced withwhat felt like a five-alarm fire.
So, this is a dramatic example.
They had customers calling or going under.
They had creditors calling or going under.
(21:30):
There were board members who wereresigning and the challenges for the board
were really at the core of their fiduciaryresponsibility, they had to preserve
the value and protect the assets and theindividuals and we had lawyers having
a heyday filing claims at that point.
But these were big board decisionsweekly; what's the fate of the business,
(21:51):
can we pivot, can we actually addressnew markets with these products?
So, what they did is they did raisecash from the largest investor.
They were able to extend their runway abit, but they also had to reduce the team
dramatically and slash expenses, and whatthey decided was that the core business
(22:11):
at the time, which was advertising, wasnot going to take them to the next stage.
Actually, this company had been builtthrough acquisitions, so a secondary
business that was embedded in the companyaround digital asset management, helping
companies launch e-commerce websites.
That actually became the core of the assetthat they decided to sell, and that was
(22:33):
the landing for this company so they wereacquired by JDA Software at that time.
I think one of the lessons from thisdecline example was that you always
need to prepare for a downside,whether it's disaster plans, whether
it's D&O insurance and for manycompanies, cash is still king.
One of Engage's top competitors,DoubleClick, had enough cash
(22:56):
to survive the downturn toultimately be acquired by Google.
You've had the opportunity toobserve these boards in every stage.
How has all of this helped you be abetter board member and, I would say
at this point, a better board chair?
I think experience in each one of thesestages helps me as a board member,
(23:18):
helps me as an investor to calibratemy support of a company to the stage
they're in and helps me to emphasizeto co-founders not only where they are,
but what stage is coming next, whatthe demands are going to be next and
what their priorities are going to be.
(23:39):
I think that type of long-termview is very helpful.
These five stages here are presentedsequentially for the ease of discussion.
Technology is changing dramatically,not only the sequence, but
the timing of these stages.
Actually, what can be done with oneengineer sitting in a cafe somewhere,
but having the whole life cycle in mind,I think helps me to appreciate what
(24:02):
the dependencies are in whatever orderit's going to work out for a company.
Chris, you used the analogy earlier in ourconversation of the gear shifting of a car
and I was struck by it that it rings true.
These five stages that you mentioned,there are various dimensions of board's
(24:23):
character that change with each ofthese stage; the size, for example,
changes, the composition changes,the hands on to a more formal nature
of responsibilities, changes, theunderlying business and it's where it
is in the cycle is what the board isthen governing and has to adapt to that.
(24:47):
You joined the ezCrater board actuallyas an executive chair, and you have
a really unique perspective andyou're still the chair of the board,
and with that, you have a reallyunique perspective on these stages.
I want to talk a little bit moreabout the role of the chair first.
How do you see it in a board, and thenyour perspective on that continuity of
(25:13):
the board chair in navigating throughall of those stages and how a board chair
may need to evolve their own role andthinking and work through these stages.
Talk about that a little bit.
Yes.
So, over the course of the 12years that I've been on the ezCater
(25:34):
board, some things have been thesame and many things have changed.
But things that have been the same isthat I view the chair role as really
a bridge between all the constituentsthat are on the board and the founders.
So, one of the things that's essentialI found through all the stages is
(25:57):
to make sure that there's alwaysregular and transparent communications
so that everyone on the boardhas a picture of what's going on.
I think the balance ofinformation is very important.
I also think it's very important thateveryone on the board has a voice.
It's not just that people have earnedit through their investment, it's
that you've selected people fortheir experience, and it's really
(26:19):
critical that they be sharing that.
Those kinds of themes, I think,are consistent throughout.
I think what's changed isthat the composition of the
board itself has changed.
In the early days, there were twofounders and an independent, and that
was a very different dynamic thanwhen we raised venture money and now
(26:39):
a third or more of the people who aresitting on the board are investors.
And then it was a different dynamicwhen we brought in independents to
help on a compensation committee,independents to help on audit committee.
So, while the complexion of the boardchanges, I think I still go by some
of those guiding principles, whichis to make sure that everyone has
visibility, everyone has a say, andwe're actively relying on board members,
(27:04):
because they've got an incredibleexperience that they can bring.
One other thing that you had mentionedearlier, Chris, is that if the board has
a choice of which investor to take themoney from, one important consideration
is who would you get as a board memberadded to the board and kind of confirming
(27:26):
and vetting that so that you have themost effective, most prudent board
that you can have for that company.
Did you also find it that way for thisjourney in various fundraising rounds?
Yes.
So, I've been on boards that I would sayare highly-functional and I would consider
ezCater a highly-functional board, andI've been on boards that were less than
(27:48):
highly-functional, and I think some of thehallmarks of the highly-functional boards,
they have at least three dimensions thatI think actually make them stand out.
They're selecting the individuals whojoin the board for three qualities.
One of them is their specific relevantexperience and knowledge, so that can
be functional, that can be domain.
But the second is a cultural fit, theyneed to actually be able to participate
(28:13):
on kind of a loving playing fieldwith the people that are on the board.
And the third, finally, is the motivation,and that's a tricky one because certainly
as you move through the stages, youhave different participants who came
with different motivations, but thereneeds to be an overlapping motivation
to support the founders and to makedecisions that are in the best interest
(28:35):
of the company and the shareholders.
I think that is kind of aconsistency, no matter what board
I've been on that's been functional.
I think when I look at boards that havebeen less than functional, a lot of boards
that are built through acquisitions, whenyou're rolling up companies, you wind
up, if you will, kind of going for a fitwith the company you're acquiring, but
(28:56):
not specifically the board member thatwould come along with that acquisition.
I think that can be very challenging attimes because you're coming from very
different DNAs and maybe very differentcultures through acquisition, and that's
something that often the board inheritsand that's maybe not the primary decision
that's being made when the company islooking to do an acquisition, but that
(29:17):
certainly does affect the complexionand that effectiveness of the board.
In a lot of ways, those three thingsare what you look for in a board
member at almost any stage of anycompany because you want the expertise,
you certainly want cultural fit.
Expertise without the fit is notgood for board composition, and why
(29:40):
is someone joining the board, andpart of what I would say, not so
much maybe in the startup, becausethere's some different aspects there.
But do you understand what therequirements of your job as a
board member are, because if youdon't understand it, you're not
likely to be a great board member.
At certain stages, what itrequires is infinite patience.
(30:04):
At another stage, it may not require that.
It may require difficult conversationsthat may require something else.
But it's funny, you're talking aboutthis particular kind of company,
and yet I think those three thingsapply to almost every kind of board.
Chris, final question, that longevityof the chair that you have that
(30:25):
super unique perspective, any tipson how people can achieve that?
Why would they keep you as theboard chair, even though the
stages of the companies varied.
How did you achieve that?
I think you'd have to ask theboard themselves and the founders.
But if I were to guess, I would say theexperience that I mentioned early on
(30:46):
and having participated in many of thesestages before, both as a board member, as
an investor and as a CEO, I think thatgave me the ability to have empathy for
what the founders were going through andto balance that with the requirements
of what the board's responsibilitiesas a fiduciary and to do a little bit
of translation between the differentskill sets that are needed on a board.
(31:11):
I think that experience was very helpful.
It's not something that we genuinelyfocused on 12 years ago, because 12 years
ago you're focused on the here and now andjust getting to the next stage, but that
could be a reason why it's worked so well.
The company ezCater continues to do great.
Chris, this was a great conversation.
Thanks so much for joining us today.
(31:33):
Really appreciate it.
Thank you, Joe and Raza.
And thank you all for listening to OnBoards with our guest, Chris Cuddy.
Please visit our websiteat OnBoardsPodcast.com.
That's OnBoardsPodcast.com.
We'd love to hear your comments,suggestions, and feedback.
And if you're not already asubscriber, please be sure to
(31:54):
subscribe at Apple Podcasts, Spotify,or wherever you get your podcasts.
And remember to leaveus a five-star review.
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your communities as best you can.
We hope you'll tune in forthe next episode of On Boards.
Thanks.
Hello, and welcome to On Boards, a deepdive at what drives business success.
I'm Joe Ayoub, and I'm herewith my co-host, Raza Shaikh.
Twice a month, On Boards is the place tolearn about one of the most critically
important aspects of any company ororganization; its board of directors
or advisors, with a focus on theimportant issues that are facing boards,
(00:28):
company leadership, and stakeholders.
Joe and I speak with a wide range ofguests and talk about what makes a board
successful or unsuccessful, what it meansto be an effective board member, and
how to make your board one of the mostvaluable assets of your organization.
Before we introduce our guest today,we want to thank the law firm of Nutter
(00:52):
McClennen & Fish who sponsored our OnBoard Summit recently in their beautiful
conference center in the Boston Seaport.
They've been incrediblepartners with us in every way.
We appreciate all they'vedone to support this podcast.
Our guest today is Chris Cuddy.
Chris has spent over 25 yearsbuilding and growing private and
(01:13):
public technology enabled companieswith an international focus.
He is board chair of ezCater, thenumber one food tech platform for
workplaces in the United States.
Chris has also served as CEO ofCheapFlights, an international travel
search engine acquired by PricelineKayak, CEO of Engage, a pioneering
(01:38):
online advertising network, now NASDAQlisted, acquired by JDA Software, and
Chief Commercial Officer at FarePortal,a leading online flight travel agency.
He has also held senior roles atCMGI, Computer Sciences Corporation,
(01:58):
Lightbridge and Goldman Sachs.
Chris was an early team member at BlueStreet Technology and Mecca Software.
He has served on the boards of public,private, and non-profit organizations,
and is an active angel investor andsupporter of early-stage companies.
(02:20):
Welcome, Chris.
Thanks so much for joiningus today on On Boards.
Well, thank you, Joeand Raza, for having me.
I admire the legacy of board membersthat you're compiling in these podcasts.
Thanks.
Chris, let's start with your background.
Can you talk about your journeyfrom Goldman Sachs to being
(02:43):
the CEO of Cheapflights?
Yes, Raza.
Well, it's a long and windingjourney, and it's really included
three different perspectives thathave shaped how I view boards.
First, I've been in the boardroom as amanagement consultant to executive teams
of large public companies for 10 yearswhen I worked at Index, and this was with
(03:05):
large public organizations; the WashingtonPost, Nielsen Media, Duke Power.
I've also been in the boardroom asan executive board member, and that
was as the CEO of public and privatetechnology companies in the US and
Europe, including Engage, which wasthe online advertising pioneer, and
Cheapflights, the online travel pioneer.
(03:25):
I've also been in the boardroomrepresenting investors when I worked
at CMGI, which was the internetincubator, and as an independent
investor with companies includingezCater, which is the only nationwide
corporate catering marketplace.
And this has been across public, private,for profit, charitable, and across
(03:45):
all stages of a company's life cycle.
That is a tremendous breadthof background, Chris.
Maybe talk a little bit moreabout the early part of ezCater.
Specifically, kind of the story of howLaunchpad, a group that you and I both
are a member of as investors, invested inezCater, and how did that journey start?
(04:10):
Yes.
Well, as you know in 2012, ezCaterwas a five-year-old company with some
incredible, really extraordinaryco-founders, Stefania Mallett and Briscoe
Rodgers, who had spent five years workingat the kitchen table on a great idea
(04:32):
to launch an online marketplace forcorporate catering and a marketplace,
you may know in many other forms, iswhen you bring together both customers
and suppliers on the same platform.
Actually, ezCater was calling itselfthe Expedia for corporate catering
just so people could understand.
And after five years, they werelooking to raise capital beyond the
(04:54):
friends-and-family rounds that they haddone and they had a lot of eagerness
to learn what they didn't know, a lotof eagerness to add some marketplace
knowledge to the board, and the board atthat time was Stefania and Briscoe and
another early independent board member,Mike Masterson, who was very experienced
in early stage CEOs in pharma and biotech.
(05:18):
Chris, was that the time when youactually joined the board post-investment,
or did you join earlier than that?
So, when ezCater came to Launchpad, theywere looking for their first organized
angel group funding round, and they didcome to the group early in their process,
(05:39):
and we launched some diligence on thecompany and spent weeks looking over
their vision, looking over their books.
Originally, Launchpad declined toinvest because the business plan was not
yet structured around the key driversfor an online marketplace, but to the
co-founder's credit, they really tookthe feedback, modified their plan, and
(06:01):
the results of that process were thatLaunchpad led the series, A&A, when Rick
Fedorowich joined as a board observerfrom Launchpad and then I joined as
the board chair, and that was a realmilestone for the company because it
was their first round of professionalfunding and the board changed composition.
This was going from a board of twofounders and one independent to now
(06:23):
a board that had two founders, twoindependents and an independent observer.
Chris, that really came about because,in part, your operator experience
in actually building marketplacesbefore, as you mentioned, for example,
the cheapflights.com was also basedon a marketplace model and that's
(06:46):
what led you to joining the board,bringing your experience to the table.
That's right.
And I think, in my experience, thisis indicative of this early stage
of a startup's life in which thedistinction between a board member and
an executive board member, a founder,can actually be very blurred, and I
(07:06):
think oftentimes the board members becomean extension of the executive team.
There are many things that in thatearly stage that I was involved in.
It was everything from interviewingteam members to working on the financial
forecasts, to working on what themodel actually was that was driving the
company, and that all happened, I think,at a frequency that was quite intense.
(07:31):
We had board meetings once a monthfor several years, but probably
more than half of the time I spentwith the board was unscheduled and
was outside of the board meetings.
So, they were ad hoc as they came up,opportunities, problems, questions,
that took the natural rhythm ofwhatever the co-founders were facing.
Yeah, it's a great point.
We talk a lot about boards and whatboard responsibilities are, and one
(07:55):
of the things that we talk about, andpretty much all our guests talk about,
is the distinction between governanceand management, but as you pointed out,
that gets blurred in some instances.
So, it would be great to spend a fewminutes, given your pretty unusual
perspective, deep and broad, infor-profit, investment-backed boards to
(08:19):
go through the stages of evolution ofa board, because it really is different
than a lot of other types of for profitand certainly non-profit companies,
so let's start with a little bitabout your perspective on watching and
observing the evolution of these boards.
(08:40):
Yes.
I think in my experience, we can usekind of the classic five stages of
a company's development, and you canmap that with what the focus of the
board is in each one of those stages.
If we go through them on the toplevel, the early seed stage for
ezCater was when they were foundersin the kitchen table, and at that
(09:01):
stage, they're basically self-funding.
They're trying to get clarity on the ideaand they may or may not have incorporated,
they may or may not have a board.
And if they do have a board, it's usuallyheavy founder based, and as I said,
even in this phase, it's very hard todistinguish board member activities
from founder activities sometimes.
But the goal there is to basicallyget the idea crystallized so they can
(09:26):
approach potential funding later on.
Yeah, I love the way you put it; ideastage, two founders and a PowerPoint.
So, it is really down to the mostbasic beginning, and then it's going
to take a lot of time, effort, luck,perseverance, super talent to even
(09:46):
get to the startup stage, whichI think is the next stage, right?
That's right.
After the seed and developmentstage, starting with two founders
and a PowerPoint, what is thenext stage that you've observed in
for-profit, investment-backed boards?
Yeah.
So, hopefully the seed and developmentstage can get followed by an actual
(10:09):
startup stage, because they'vecrystallized what their idea is,
they've got a business plan or at leastthe first version of that, and they
really want to go to a stage wherethey can focus on clarifying the early
product market fit where they canmake sure that they have a business
(10:30):
that they could pitch to investors.
At that stage, they might be lookingto raise their first organized angel
round, which is where we met ezCater.
And what does it take for them at thisstage to validate their business model?
What do they have to show the investorsand maybe their board in order to
(10:51):
actually succeed at that stage?
Their proof points that are super helpfulat this stage are anything that they
can show that convinces an investorthat they've got early product market
fit and that they've got a repeatablemodel that's actually going to scale.
So, this means that they've got customerfeedback, this means that they've got
(11:13):
supplier feedback, and they can showthat these are not just one offs,
they can show that they've actuallytapped into a vein of need and they're
uniquely providing some value for that.
And the board's role is still kind ofblurred between governance and management?
I mean, you're still workingwith management to get
through the startup stage.
(11:34):
Is that right?
Yes.
And even to the point where in this stageI've been doing customer calls, going door
to door with a sales rep to really try tosense if the model is getting traction.
So, it can be wearing many hats.
It can be actually workingon financial forecasts.
It can be actually coaching the CEO.
(11:56):
Many times when you've got co-founders,they have worked together before and
many times they have not, and very oftenthe roles that they're in are roles that
they're taking for the first time, andbeing the first time CEO, they could
really use the guidance of someone who'sbeen in that role before, and that's
(12:17):
often one of the most helpful things thatyou're doing because it's really a grab
bag of whatever is on the founder's mindand whatever hurdles they're coming across
at any given day for you to be able tostep in and either give them guidance,
give them a hand or direct them to someresources that you know that can help.
So, it's really all hands on deckas far as the board is concerned and
(12:38):
helping them validate the model so theycan get to the growth stage, which is
the next stage, is that about right?
That's right.
And I would say that between the firsttwo stages, the seed and the startup,
it's still a very fragile environment,and one of the things as a board
member that I think it's importantto remember is that investors, board
members are attracted to a company inthese first two stages, in large part,
(13:01):
because of the founders themselves.
They don't yet have cash flow.
They don't yet have an idea thathas been proven beyond a doubt.
You're really drawn to the individualswho are on that founding team, and
it's very important to remember thatand to listen to them because that's
what attracted you in the first place.
So, I think I consider myself a fastfollower and maybe anticipating what's
(13:23):
going on, but that's a differencebetween putting a hand on the steering
wheel, and I think if you get to thatsituation, then you have to step back
and question whether this is the rightopportunity for you as a board member.
Yeah, that is a great point, thatyou really still have to keep the
focus on the fact that you're therebecause of the founder or founders,
(13:45):
and that listening to them isimportant if you're going to help them.
Yes.
Yeah.
So, the next stage is the growth stage.
What does that entail?
What does it look like, and what's themoney aspect that have you now grown?
Is it out of angel into VC?
Is it something else?
Yes.
That the characteristics of thegrowth stage are when the founders
(14:08):
and the founding team has some earlycustomer and financial success with
some increased predictability now andthey've really proven that they have
the potential to accelerate growth.
So, at this stage, they're lookingto ramp up operations, and that very
often requires additional funding.
I'll continue on the ezCater example.
(14:30):
They had been chasing a huge opportunityin the first two stages of their
growth, but they didn't feel like theywere moving fast enough, even though
as the founder says their growthrates had growth rates at that time.
They didn't feel like they weredoing everything they could.
They thought it would be a very longjourney to actually go state by state
and caterer by caterer on the angel groupfunding levels that they've raised so far.
(14:54):
So, at that point, the board wasasking, how can they accelerate growth?
What would be the fastest way tooffer catering in all 50 states, and
what if capital wasn't a constraint?
And the answer that they reached is,I think, very typical for the growth
stage, which is that the ambition andthe timeframes that they were talking
about required venture capital, andthat was a big conversation because
(15:18):
the founders had prided themselvesup to this point on frugality.
So, the board went through somereal soul searching about would
this change the DNA of the company?
Would we lose control?
Or can we take on morepartners and satisfy everyone?
So, I think that's a very emblematic,dynamic of this stage, and for ezCater
(15:40):
at least, the board did approvethis ambitious path that was venture
funding enabled, and basically kickedoff a process of reaching out to VCs,
which winds up being a heavy liftfor some co-founders who are managing
the business in the daytime and atnight, they're getting introduced to
VCs, they're exploring them, they'rereaching out, interviewing, and
(16:03):
the whole process of that entails.
Is the board composition stillpretty similar to the way
it was in the startup stage?
It hasn't really shifted until theVCs come on or new investors come on.
Is that right?
Or is it already changing?
That's my experience.
I think the board at thisstage was co-founders when
(16:24):
they were in the seed stage.
They maybe brought on some angelswhen they were in the startup
stage, but it's still a board thatis maybe four or five people and
you're still wearing multiple hats.
I think the growth stage is really whenyou're injecting a degree of formality.
Now, this is when you need toformalize an audit committee.
If you haven't had a comp committeealready, you need to put that in place.
(16:47):
Because the venture model has a rhythmto it, and it has some standards to
it, and it's going to require reportinglevels that you may be as a co-founder
haven't been delivering to your investorsas frequently with the same rigor.
From the growth stage to the nextstage which you call maturity, what is
(17:07):
happening, and what would define whatgets you to the so-called mature stage?
Yeah.
In the growth stage, one of the things Ithink to remember every time you've added
people to the board is that these arelife changing decisions for the founders
and these are multi-year relationshipsthat you're reaching out to create.
(17:28):
Before you leave the growth stage,it's very important to build the board
intentionally with that long-term view andreally make sure that you're building a
board where people have not only a domainexperience that they can bring, not only a
cultural fit, but also people who have thesame intention, and that will very much
help you to get through the growth phase.
(17:49):
By the time you get to maturity, thisis for most businesses many, many
years out, and this is when you've gotpredictable and stable revenue and a
strong brand, and at this point, theboard structure should be humming along
and this is really all about execution.
Is this board at maturity now, morereflective of what we think of as the
(18:13):
kind of board roles that are most common?
In other words, you're not sittingdown late at night with the
founders anymore, or maybe you are.
Is it more governance and lessday-to-day kind of work that is very
much part of what management is doing.
Yes, maturity level for companies iswhen the board gets into the rhythm,
(18:36):
they get into the cadence, you havecommittees, you've got responsibilities,
you've got succession planning going on.
So, the structure of the companynow is well understood, and as
far as the board's going, it feelsmore like a maintenance mode than a
putting out fires and running aroundsupporting every founder's activity.
(18:58):
Are the founders still on the board,number one, and number two, are you
able to look around at this point forindependents who are not necessarily
investors that can come in because theyhave something in their background;
it may be domain experience, maybe operational, it may be something
else that is critical to the successof this company at a mature stage?
(19:22):
Yes.
especially from mature companies thathave gone to the public markets at
this stage, you're definitely goingto be looking at a full-fledged board.
You're going to have independents inthe appropriate ratios and this is
a real now stable, kind of reliablecomponent of the organization that
is distinct from the management team.
(19:43):
I think it's at this mature stagewhere for the first time you see the
clear delineation of those two roles.
And the last stage that you have, Ilove the way it is, it says renewal
decline, which makes me think you cango either way, and it also makes me
think that these five stages is partof a cycle that can now repeat itself.
(20:06):
Because if there's a decline, then I wouldguess there are things you do to get back
to growth or get back to some other stage.
Can you just talk a bit once there'smaturity, how do you keep it going?
How do you either address the declineor make sure that you're renewing it,
energizing it, making sure it's wellfunded, well governed, et cetera.
(20:28):
They fall into this renewal and decline.
For some, they're able to rejuvenatethemselves and for some, they're not.
I can actually give a story of onethat that was not able to do it.
This is a company that was very highgrowth that had intense competition.
This company was called Engage.
It was a public company on the NASDAQ,and it was one of the high flying
(20:49):
pioneers of the online advertising space.
They had an incredible product wherethey could do anonymous profiling.
They could serve you an ad specificallytargeted to you without having any
personally identifiable information.
It was great and things weregoing well when they ran into
the Internet bubble bursting.
(21:10):
So, this was not of their ownmaking as much as they got caught
up in really economic headwindsthat turned into a downturn.
So, the board was really faced withwhat felt like a five-alarm fire.
So, this is a dramatic example.
They had customers calling or going under.
They had creditors calling or going under.
(21:30):
There were board members who wereresigning and the challenges for the board
were really at the core of their fiduciaryresponsibility, they had to preserve
the value and protect the assets and theindividuals and we had lawyers having
a heyday filing claims at that point.
But these were big board decisionsweekly; what's the fate of the business,
(21:51):
can we pivot, can we actually addressnew markets with these products?
So, what they did is they did raisecash from the largest investor.
They were able to extend their runway abit, but they also had to reduce the team
dramatically and slash expenses, and whatthey decided was that the core business
(22:11):
at the time, which was advertising, wasnot going to take them to the next stage.
Actually, this company had been builtthrough acquisitions, so a secondary
business that was embedded in the companyaround digital asset management, helping
companies launch e-commerce websites.
That actually became the core of the assetthat they decided to sell, and that was
(22:33):
the landing for this company so they wereacquired by JDA Software at that time.
I think one of the lessons from thisdecline example was that you always
need to prepare for a downside,whether it's disaster plans, whether
it's D&O insurance and for manycompanies, cash is still king.
One of Engage's top competitors,DoubleClick, had enough cash
(22:56):
to survive the downturn toultimately be acquired by Google.
You've had the opportunity toobserve these boards in every stage.
How has all of this helped you be abetter board member and, I would say
at this point, a better board chair?
I think experience in each one of thesestages helps me as a board member,
(23:18):
helps me as an investor to calibratemy support of a company to the stage
they're in and helps me to emphasizeto co-founders not only where they are,
but what stage is coming next, whatthe demands are going to be next and
what their priorities are going to be.
(23:39):
I think that type of long-termview is very helpful.
These five stages here are presentedsequentially for the ease of discussion.
Technology is changing dramatically,not only the sequence, but
the timing of these stages.
Actually, what can be done with oneengineer sitting in a cafe somewhere,
but having the whole life cycle in mind,I think helps me to appreciate what
(24:02):
the dependencies are in whatever orderit's going to work out for a company.
Chris, you used the analogy earlier in ourconversation of the gear shifting of a car
and I was struck by it that it rings true.
These five stages that you mentioned,there are various dimensions of board's
(24:23):
character that change with each ofthese stage; the size, for example,
changes, the composition changes,the hands on to a more formal nature
of responsibilities, changes, theunderlying business and it's where it
is in the cycle is what the board isthen governing and has to adapt to that.
(24:47):
You joined the ezCrater board actuallyas an executive chair, and you have
a really unique perspective andyou're still the chair of the board,
and with that, you have a reallyunique perspective on these stages.
I want to talk a little bit moreabout the role of the chair first.
How do you see it in a board, and thenyour perspective on that continuity of
(25:13):
the board chair in navigating throughall of those stages and how a board chair
may need to evolve their own role andthinking and work through these stages.
Talk about that a little bit.
Yes.
So, over the course of the 12years that I've been on the ezCater
(25:34):
board, some things have been thesame and many things have changed.
But things that have been the same isthat I view the chair role as really
a bridge between all the constituentsthat are on the board and the founders.
So, one of the things that's essentialI found through all the stages is
(25:57):
to make sure that there's alwaysregular and transparent communications
so that everyone on the boardhas a picture of what's going on.
I think the balance ofinformation is very important.
I also think it's very important thateveryone on the board has a voice.
It's not just that people have earnedit through their investment, it's
that you've selected people fortheir experience, and it's really
(26:19):
critical that they be sharing that.
Those kinds of themes, I think,are consistent throughout.
I think what's changed isthat the composition of the
board itself has changed.
In the early days, there were twofounders and an independent, and that
was a very different dynamic thanwhen we raised venture money and now
(26:39):
a third or more of the people who aresitting on the board are investors.
And then it was a different dynamicwhen we brought in independents to
help on a compensation committee,independents to help on audit committee.
So, while the complexion of the boardchanges, I think I still go by some
of those guiding principles, whichis to make sure that everyone has
visibility, everyone has a say, andwe're actively relying on board members,
(27:04):
because they've got an incredibleexperience that they can bring.
One other thing that you had mentionedearlier, Chris, is that if the board has
a choice of which investor to take themoney from, one important consideration
is who would you get as a board memberadded to the board and kind of confirming
(27:26):
and vetting that so that you have themost effective, most prudent board
that you can have for that company.
Did you also find it that way for thisjourney in various fundraising rounds?
Yes.
So, I've been on boards that I would sayare highly-functional and I would consider
ezCater a highly-functional board, andI've been on boards that were less than
(27:48):
highly-functional, and I think some of thehallmarks of the highly-functional boards,
they have at least three dimensions thatI think actually make them stand out.
They're selecting the individuals whojoin the board for three qualities.
One of them is their specific relevantexperience and knowledge, so that can
be functional, that can be domain.
But the second is a cultural fit, theyneed to actually be able to participate
(28:13):
on kind of a loving playing fieldwith the people that are on the board.
And the third, finally, is the motivation,and that's a tricky one because certainly
as you move through the stages, youhave different participants who came
with different motivations, but thereneeds to be an overlapping motivation
to support the founders and to makedecisions that are in the best interest
(28:35):
of the company and the shareholders.
I think that is kind of aconsistency, no matter what board
I've been on that's been functional.
I think when I look at boards that havebeen less than functional, a lot of boards
that are built through acquisitions, whenyou're rolling up companies, you wind
up, if you will, kind of going for a fitwith the company you're acquiring, but
(28:56):
not specifically the board member thatwould come along with that acquisition.
I think that can be very challenging attimes because you're coming from very
different DNAs and maybe very differentcultures through acquisition, and that's
something that often the board inheritsand that's maybe not the primary decision
that's being made when the company islooking to do an acquisition, but that
(29:17):
certainly does affect the complexionand that effectiveness of the board.
In a lot of ways, those three thingsare what you look for in a board
member at almost any stage of anycompany because you want the expertise,
you certainly want cultural fit.
Expertise without the fit is notgood for board composition, and why
(29:40):
is someone joining the board, andpart of what I would say, not so
much maybe in the startup, becausethere's some different aspects there.
But do you understand what therequirements of your job as a
board member are, because if youdon't understand it, you're not
likely to be a great board member.
At certain stages, what itrequires is infinite patience.
(30:04):
At another stage, it may not require that.
It may require difficult conversationsthat may require something else.
But it's funny, you're talking aboutthis particular kind of company,
and yet I think those three thingsapply to almost every kind of board.
Chris, final question, that longevityof the chair that you have that
(30:25):
super unique perspective, any tipson how people can achieve that?
Why would they keep you as theboard chair, even though the
stages of the companies varied.
How did you achieve that?
I think you'd have to ask theboard themselves and the founders.
But if I were to guess, I would say theexperience that I mentioned early on
(30:46):
and having participated in many of thesestages before, both as a board member, as
an investor and as a CEO, I think thatgave me the ability to have empathy for
what the founders were going through andto balance that with the requirements
of what the board's responsibilitiesas a fiduciary and to do a little bit
of translation between the differentskill sets that are needed on a board.
(31:11):
I think that experience was very helpful.
It's not something that we genuinelyfocused on 12 years ago, because 12 years
ago you're focused on the here and now andjust getting to the next stage, but that
could be a reason why it's worked so well.
The company ezCater continues to do great.
Chris, this was a great conversation.
Thanks so much for joining us today.
(31:33):
Really appreciate it.
Thank you, Joe and Raza.
And thank you all for listening to OnBoards with our guest, Chris Cuddy.
Please visit our websiteat OnBoardsPodcast.com.
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(31:54):
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