Category Archives: Leadership

Is a Dream a Lie if It Don’t Come True? Founders, Aspirations, and Company Potential

“Is a dream a lie if don’t come true?” — Bruce Springsteen

The River was one of my favorite songs in college and whenever I listen to the above line near the end, I start thinking about Silicon Valley.

Consider three entrepreneurs.

Founder 1:  Elizabeth Holmes.  Was she simple con artist who chose fraud over business failure or a broken visionary trying to walk in the footsteps of Steve Jobs?

Founder 2:  Adam Neumann who dressed up the equivalent of Regus as a tech company and successfully raised money at valuations up to $47B before flaming out on the approach to an IPO.  (Now seemingly running a similar play with Flow.)

Founder 3:  Joe, our friend at BigCo who quit his VP-level job to found a company, spent 10 years sweating it out, pivoted, recapped, and finally threw in the towel for a carve-out in a $30M sale that didn’t clear the preference stack.

Which are they?  Were they dreamers or liars?

To try and sort that out, I’d consider three questions:

  • Did they truly believe in the dream?  It’s hard to know what anyone truly believes [1] — and we need to separate visionaries from lunatics [2] — but in many situations you can develop a sense for whether someone is a true believer or a poser.  This one’s hard to assess, but important.
  • Were they lying about progress?  While there is a small gray zone of exaggeration, misunderstanding, and embellishment [3], for the most part this one is black and white.  Were the numbers real?  Was the demo faked?  Were the milestones hit?
  • Were they making big money before realizing the dream?  This didn’t used to be possible in Silicon Valley, but a side effect of the recent financing environment [4] was the rise of secondary sales that made it possible for founders to reap 10s to 100s of millions before a liquidity event that shared success more broadly across investors and employees.  Situations where a founder can make “done” (or “lifestyle changing”) money before realizing the dream can present the potential for conflicts of interest.

We ask a lot from founders.  And what we ask is often in diametric oppposition.   We ask founders to be:

  • Unreasonable, but reasonable.  Founding a startup against long odds is an inherently unreasonable thing to do.  But, aside from that, we want them to be reasonable people.
  • Optimistic, but realistic.  We want them to believe they can accomplish the nearly impossible, but be realisitic in setting goals and operating plan targets.
  • Big-picture, but detail-oriented.  We want them to create a disruptive, big-picture vision of the market, but be able recite SaaS metrics from memory.

This alone is a good reason to have both co-founders and a strong executive team.  While F Scott Fitzgerald said, “the test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time,” it’s hard to do so in every situation, all the time.

While plenty has been written about Holmes and Neumann inspired a TV series, nobody talks much about Joe.   And there are a lot of Joe’s out there.

Joe’s employees and investors are disappointed in him and might be mad at him.  After all, Joe probably said:

  • The company faced an amazing opportunity
  • The space had the potential to produce a public company
  • He believed they could beat BadCo and WorseCo to win the market

But what did we want Joe to say?   Yes, Joe needs to be careful.  He needs to speak precisely and make precise claims.  He needs to hedge his language and not make promises.  But Joe is not only allowed to be optimistic, it’s his job.

As I’ve often said,

“As CEO, even if you’re standing neck-deep in shit, you need to be looking at the stars.”

Put differently, while the CEO needs to be aware of the company’s situation and have credible plans to address it (i.e., the neck-deep part), they must always be focused on and believe in the potential of the company [5].  The day they can’t do that is when they should turn in their badge.

So, going back to Springsteen, “is a dream a lie if it don’t come true — or is it something worse?”

# # #

Notes

[1]  I’d argue it’s sometimes easier to know when they don’t — e.g., if they’re telling all their friends they’re running a scam.

[2] For example, the difference between trying to emulate Steve Jobs and thinking that you have been sent by God as the reincarnation of Steve Jobs.

[3] Larry Ellison reportedly once said, “sometimes I just get my verb tenses mixed up” when speaking about product capabilities vs. roadmap.

[4] E.g., higher valuations, longer time to liquidity, higher bar on IPOs.

[5] My take on what’s known as the Stockdale paradox.

The Decomposition of Marketing

To adapt Julius Caesar’s famous opening line of the Gallic Wars:  marketing as a whole is divided in three parts.

  • Product marketing (prodmkt), responsible in a word, for the message and how well it resonates with customers in the market [1].
  • Demand generation (demandgen), responsible in a word, for generating opportunities (oppties) to feed sales [2].
  • Corporate communications (corpcomm), responsible in a word, for communications, including branding, public relations, and corporate-level messaging [3].

Two important notes:

  • There is an optional fourth part, sales development, i.e., managing the team of sales development reps (SDRs) who convert MQLs into stage-1 oppties.  Whether this team should report into sales or marketing is a separate debate.
  • The lines between these parts are not black and white.  Social media advertising is demandgen, but posting is either comms or prodmkt.  Prodmkt helps provide content for demandgen campaigns.  Content marketing is a form of light prodmkt.

Marketing leaders grow up [4] in one of those parts and thus take one of the three basic flavors. But just as few CFOs grew up in legal, few CMOs grew up in corpcomm.  So it really comes down to two:  most CMOs either grew up in product marketing or demandgen (just as most CFOs either grew up in either finance or accounting).  The point being that virtually no one grew up in both.

It was this realization that led me to create “pillar profiles” for marketers — a score from 1-5 on each of the three (plus one) pillars of marketing: prodmkt, demandgen, corpcomm, and sales development.  The trick is you only get a maximum of 15 points to assign [4a].  While I’ve never blogged on pillar profiles, I did cover them in my SaaStr 2021 talk, A CEO’s Guide to Marketing.

If you’re searching for a CMO, the first thing you should do is identify your target pillar profile [5].  Remember that you get a maximum of 15 points and, harder yet, you’ll find that {5, 4, x, x} and {4, 5, x, x} candidates are very hard to come by.  Usually you’ll find {5, 3, x, x} and {3, 5, x, x} candidates.

In the past, this forced startup CEOs to choose between a prodmkt- and a demandgen-oriented head of marketing.  But, with marketing ever more accountable for building pipeline [6], it was a Hobson’s choice:  most picked demandgen-oriented leaders because without pipeline, well, everything stops.  It’s the physiological needs level of marketing.

Increasingly though, I see startup CEOs interested in changing the rules so they have both strong prodmkt and demandgen leadership.  They’re doing this by decomposing marketing and reconstituting it in various ways:

  • Generally hiring demandgen-oriented CMOs [7].
  • Moving product marketing to report into either the chief product officer (CPO) or the CEO directly.
  • Occaisionally moving demandgen under the CRO, leaving behind either a prodmkt-oriented CMO or additionally putting prodmkt under product, leaving a corpcomm-oriented CMO.

I think all of these options can work in different situations, so let’s review the pro/cons of four different marketing org structures [8].

New, Traditional Marketing Structure
I believe the new traditional structure [9] is to hire a demandgen-oriented CMO and put prodmkt under that CMO.

The new, traditional marketing structure. Demandgen-oriented CMO with prodmkt reporting in.

The strength is that you get to hire a strong demandgen leader in the CMO slot and they will likely do well at filling the pipeline.  It may, however, be difficult to attract the level of prodmkt leader that you want because they may feel like “they understand the business bettter than their boss,” even if they lack the demandgen skills required for into the CMO role.

Prodmkt Under Product Structure
In this structure, your hire a demandgen-oriented CMO and move prodmkt under product.

Prodmkt under Product marketing structure. Demandgen-oriented CMO who also runs comms.

The strength here is that you get to hire a strong demandgen leader as CMO and — if you happen to have the right CPO — then prodmkt can work quite effectively under product.  This works best when the CPO is a great outbound communicator who has both a genuine interest and prior experience in prodmkt.  Never, ever force-fit this.  Some product leaders just want to manage the backlog [10].  I would note that large-company general manager (GM) positions, e.g., the one I held at Salesforce, are effectively “product management on steroids” and those steroids include taking over a lot of product marketing duties.  In such organizations, product marketing also exists outside the business units, but it is staffed at a lower ratio, and more product-line and campaigns-support in nature.

Prodmkt Under CEO Structure
Here again you hire a demandgen-oriented CMO but move prodmkt directly under the CEO, instead of under the CPO.

Prodmkt reporting to CEO structure. A demandgen-oriented CMO runs DG and comms.

I like this structure for early-stage startups because it lets the CEO have their cake and eat it, too — i.e., they can attract strong demandgen and prodmkt leaders.  This structure also keeps the CEO close to the action during the early days when the company is still evolving its message frequently.  It gives the CMO a chance to keep their job while still subtly giving the VP of Prodmkt the chance to earn the CMO job if they work well with the CEO, crush the prodmkt role, and demonstrate significant understanding of demandgen [11].  A little internal competition keeps everyone on their toes.

Fully Decomposed Structure
Fewer people contemplate this structure, but I have seen it once or twice.  Here you move demandgen under sales, prodmkt under product, and hire a corpcomm-oriented head of marketing.

Fully decomposed with DG under sales, prodmkt under product, and a corpcomm-oriented CMO

I’m generally not a fan of this structure because I don’t like marketing reporting into sales [12].  The strength is theoretically alignment:  by putting demandgen under sales, the CEO can effectively delegate responsibility for aligning demandgen to the CRO.  This structure may work for product-oriented founders who have little interest in go-to-market (GTM) functions [13].  The weakness here will be potential difficultly in finding good people to staff both the head of demandgen and the head of prodmkt roles.  Additionally, I’d guess that only 1 in 5 CPOs are good fits to run prodmkt.

Conclusion
In this post, we covered several topics:

  • The idea that marketing fundamentally has three parts — product, demandgen, and corpcomm — and that sometimes there’s an optional fourth, sales development.
  • That we can and should make pillar profiles to identify, at the start of a CMO search, which pillar profile we are looking for.
  • That startup CEOs are increasingly exploring alternative organizational structures to have their cake and eat it, too, when it comes to hiring marketing talent.
  • We examined four different structures and quickly discussed the strengths and weaknesses of each.

# # #

Notes
[1] A more detailed list:  positioning, messaging, high-value content (e.g., collateral), sales tools and training, support for public relations (PR) and analyst relations (AR).  Because the latter is fairly product-focused and time-intensive (e.g., extensive RFPs, briefings, and demos), you increasingly see AR split from PR and often reporting into product marketing.

[2] I contemplated, but deliberately did not pick “pipeline,” because sales must be responsible for the pipeline.  I could have said “generating pipeline,” but that’s two words and marketing is only one of four sources for so doing.

[3] As companies get larger and have multiple products, the need emerges for a corporate-level capstone message that transcends product line messages.  Note that I contemplated but deliberately avoided chosing “brand” as the single word, because it’s highfalutin for an early-stage startup.  See my post, practical thoughts on branding.

[4] Meaning specifically, had their formative career experiences working in and thus both have a deep knowledge of and the embedded point of view of that given department.  Finance people generally look at the company differently than accounting people.  Ditto for product marketers and demandgen people.

[4A] On the rough theory that, “the universe doesn’t make those,” so if you’re actually going to hire someone you need to realize that even 15 points is a pretty good score.

[5] As a board member, nothing is a bigger red flag on a marketing search than when the three finalists bear no resemblance to each other, e.g., a {5, 3, 3, 2}, a {2, 5, 3, 4}, and a {2, 3, 5, 3}.  If you need a {2, 5, 3, 4} then all finalists should be pretty close to that pillar profile.  You’ve effectively deferred deciding what you need until picking, which wastes time and changes your final decision from, “of the three people who look like what we need, which one is best for us,” to “what type of person do we need again?”

[6] It may be hard to believe but 25 years ago, before the widespread adoption of CRM, marketing had largely tactical and poorly measured responsibilities on lead generation.  Here’s my take on the evolution of software marketing.

[7] While I know early-stage startups don’t often have CXO-style titles, please consider CXO here to be a compact notation for saying “VP of <function>” or “Head of <function>”.

[8] I’ll leave the SDR question to the side as I view it as orthogonal and addressed in this post.

[9] I suppose I could just say contemporary, but “new, traditional” strikes me as more precise.  It’s now the “traditional” way, but yes, it’s still fairly “new” from where I sit.  Neotraditional doesn’t work as that means a new adaptation of a traditional thing.

[10] Becoming an incrementalist is the occupational hazard of a career in product management.

[11] In which case the CMO would have no functional job change but get put under the prodmkt leader. If this is a possiblity far better to call one VP of Prodmkt and the other VP of Marketing, so when that occurs it’s a promotion to CMO for one of them, but not a demotion for the other.

[12] There is no doubt some religion in my dislike, having been CMO of three companies for over a decade.  I think the rational argument is that you don’t need to put marketing under sales to align marketing with sales, and such, doing so is rather a brute-force approach that will result in a smaller candidate pool.  Moreover, most CROs know little about marketing and are not able to add much value when they manage it.

[13] Of course my general advice is to develop that interest.  The typical SaaS company spends twice on S&M what it spends on R&D.  Thus, while you may think you founded a product company, you actually founded a distribution business.  So go figure it out!  (And it’s fun.)

Preview of My SaaStr Europa Talk: The Top 5 Scale-Up Mistakes

I’ll be speaking next month in Barcelona on the first day of SaaStr Europa, held at the International Convention Center on June 7th and 8th.   My presentation is scheduled at 11:25AM on June 7th and entitled The Top 5 Scale-Up Mistakes and How to Avoid Them.  While I usually speak at SaaStr, this is my first SaaStr Europa, and I’ll be making the trip over in my capacity as an EIR at Balderton Capital.

For those concerned about Covid, know that SaaStr Europa, like its Silicon Valley namesake, is a primarily outdoor and open air conference.  I spoke at SaaStr Annual in Silicon Valley last September and between the required entry testing and the outdoor venue felt about as safe as one could in these times.  Earlier this year, the folks at SaaStr moved the Europa venue from London to Barcelona to enable this primarily outdoor format.

After historically focusing a lot of my SaaStr content on the start-up phase (e.g., PMF, MVP), this year I thought I’d move to scale-up, and specifically the things that can go wrong as you scale a company from $10M to $100M in ARR.  Even if your company is still below $10M, I think you’ll enjoy the presentation because it will provide you with a preview of what lies ahead and hopefully help you avoid common mistakes as you enter the scale-up stage.  (If nothing else, the rants on repeatability and technical debt will be worth the price of admission!)

Without excessively scooping myself, here’s a taste of what we’ll talk about in the presentation:

  • Premature go-to-market acceleration.  Stepping on the gas too hard, too early and wasting millions of dollars because you thought (and/or wanted to believe) you had a repeatable sales model when you didn’t.  This is, by far, the top scale-up mistake.  Making it costs not only time and money, but takes a heavy toll on morale and culture.
  • Putting, or more often, keeping, people in the wrong roles.  Everybody knows that the people who helped you build the company from $0 to $10M aren’t necessarily the best people to lead it from $10 to $100M, but what do you do about that?  How do you combine loyalists and veterans going forward?  What do you do with loyalists who are past their sell-by date in their current role?
  • Losing focus.  At one startup I ran, I felt like the board thought their job was to distract me — and they were pretty good at it.  What do you do when the board, like an overbearing parent, is burying you in ideas and directive feedback?  And that’s not mention all the other distraction factors from the market, customers, and the organization itself.  How does one stay focused?  And on what?
  • Messing up international (USA) expansion.  This is a European conference so I’ll focus on the mistakes that I see European companies make as they expand into the USA.  Combining my Business Objects experience with my Nuxeo and Scoro board experience with both Balderton and non-Balderton advising, I’m getting pretty deep on this subject, so I’m writing a series on it for the Balderton Build blog.  This material will echo that content.
  • Accumulating debilitating technical debt.  “I wear the chain I forged in life,” said Jacob Marley in A Christmas Carol and so it is with your product.  Every shortcut, every mistake, every bad design decision, every redundant piece of code, every poor architectural choice, every hack accumulates to the point where, if ignored, it can paralyze your product development.  Pick your metaphor — Marley’s chains, barnacles on a ship, a house of cards, or Fibber McGee’s closet — but ignore this at your peril.  It takes 10-12 years to get to an IPO and that’s just about the right amount of time to paralyze yourself with technical debt.  What can you do to avoid having a product crisis as you approach your biggest milestone?

For those in attendance, we will have an Ask Me Anything (AMA) session after the presentation.  I’ll post my slides and the official SaaStr video after the conference.

This should be fun.  I hope to see you there!

An Epitaph for Intrapreneurship

About twenty years ago, before I ran two startups as CEO and served as product-line general manager, I went through an intrapreneurship phase, where I was convinced that big companies should try to act like startups.  It was a fairly popular concept at the time.

Heck, we even decided to try the idea at Business Objects, launching a new analytical applications division called Ithena, with a mission to build CRM analytical applications on top of our platform.  We made a lot of mistakes with Ithena, which was the beginning of the end of my infatuation with the concept:

  • We staffed it with the wrong people.  Instead of hiring experts in CRM, we staffed it largely with experts in BI platforms.  Applications businesses are first and foremost about domain expertise.
  • They built the wrong thing.  Lacking CRM knowledge, they invested in building platform extensions that would be useful if one day you wanted to build a CRM analytical app.  From a procrastination viewpoint, it felt like a middle school dance.  Later, in Ithena’s wreckage, I found one of the prouder moments of my marketing career  — when I simply repositioned the product to what it was (versus what we wanted it to be), sales took off.
  • We blew the model.  They were both too close and too far.  They were in the same building, staffed largely with former parent-company employees, and they kept stock options in both the parent the spin-out.  It didn’t end up a new, different company.  It ended up a cool kids area within the existing one.
  • We created channel conflict with ourselves.  Exacerbated by the the thinness of the app, customers had trouble telling the app from the platform.  We’d have platform salesreps saying “just build the app yourself” and apps salesreps saying that you couldn’t.
  • They didn’t act like entrepreneurs.  They ran the place like big-company, process-oriented people, not scrappy entrepreneurs fighting for food to get through the week.  Favorite example:  they had hired a full-time director of salesops before they had any customers.  Great from an MBO achievement perspective (“check”).  But a full-time employee without any orders to book or sales to analyze?  Say what you will, but that would never happen at a startup.

As somebody who started out pretty enthralled with intrapreneurship, I ended up pretty jaded on it.

I was talking to a vendor about these topics the other day, and all these memories came back.  So I did quick bit of Googling to find out what happened to that intrapreneurship wave.  The answer is not much.

Entrepreneurship crushes intrapreneurship in Google Trends.  Just for fun, I added SPACs to see their relatively popularity.

Here’s my brief epitaph for intrapreneurship.  It didn’t work because:

  • Intrapreneurs are basically entrepreneurs without commitment.  And commitment, that burn the ships attitude, is key part of willing a startup into success.
  • The entry barriers to entrepreneurship, particularly in technology, are low.  It’s not that hard (provided you can dodge Silicon Valley’s sexism, ageism, and other undesirable -isms) for someone in love with an idea to quit their job, raise capital, and start a company.
  • The intrapreneurial venture is unable to prioritize its needs over those of the parent.  “As long as you’re living in my house, you’ll do things my way,” might work for parenting (and it doesn’t) but it definitely does not work for startup businesses.
  • With entrepreneurship one “yes” enables an idea, with intrapreneurship, one “no” can kill it.  What’s more, the sheer inertia in moving a decision through the hierarchy could kill an idea or cause a missed opportunity.
  • In terms of the ability to attract talent and raise capital, entrepreneurship beats intrapreneurship hands down.  Particularly today, where the IPO class of 2020 raised a mean of $350M prior to going public.

As one friend put it, it’s easy with intrapreneurship to end up with all the downsides of both models.  Better to be “all in” and redefine the new initiative into your corporate self image, or “all out” and spin it out as an independent entity.

I’m all for general mangers (GMs) acting as mini-CEOs, running products as a portfolio of businesses.  But that job, and it’s a hard one, is simply not the same as what entrepreneurs do in creating new ventures.  It’s not even close.

The intrapreneur is dead, long live the GM.

What Exactly Do You Mean by Anal? Thoughts on Leadership and Self-Awareness

I remember one time having an argument that went like this:

Dave:  I don’t think you’ve thought through the details on this one.

Joe:  I think there’s enough detail in there.

Dave:  No, there’s not.  There’s no underpinnings, there’s no rigor in the thought process.  Remember, David Ogilvy always said “good writing is slavery” and ergo you need to dive deep and —

Joe:  Oh, you can be so anal.

Dave:  I don’t think I’m being anal.  I’m just being rigorous.

Joe:  Yes, you are.

Dave:  Well, what exactly do you mean by anal?

I always try to listen to myself and once in a while I have a did-I-just-say-that moment.  Did I just say, “what exactly do you mean by anal?”  Oh shit, I did.  Isn’t that kind of the definition of being anal?  Oh shit, it is.  Heck Dave, you may as well just have replied:  what I really want to know is — is there a hyphen in anal-retentive?

The actual issue here is one of leadership:  being aware of your strengths and weaknesses, trying to avoid over-doing your strengths and working to compensate for your weaknesses.  It’s critical that all leaders focus on this because, by default, most folks will over-play to their strengths (to a fault, effectively turning them into weaknesses) and ignore their weaknesses.

It’s not hard to be self-aware when it comes to most strengths and weaknesses.  Most folks know, for example, if they’re great at public speaking and bad at financial analysis, or great at individual problem-solving but bad in groups.  Or high on IQ but low on EQ.  People usually know.

Sometimes we euphemize with ourselves.  For example, while others might say I’m:

  • Detail-oriented, I prefer “rigorous”
  • Blunt, I prefer “direct”
  • Contrarian, I prefer “critical-thinking”
  • And so on

But at least you’re circling the same pond.  You have awareness of the area –though you might soften how you think about it to protect the old ego, relative to how others might more bluntly, or should I say directly, describe it.

But some weaknesses are harder to self-assess.  For example, I’ve taken assessments that basically prove I’m low on flexibility.  But I never knew it.  In fact, I thought I was supremely flexible because I was capable of moving.  Think:  OK, we’ll move a bit in your direction.  You see, I’m flexible!  Voila, QED.  Bravo Chef!  I was, however, blind to the fact that one person’s mile is another’s inch.  When you’re inflexible you risk self-congratulation for a tidbit of demonstrated movement when the other party thinks you haven’t moved at all.

As another example, because communication is one of my strengths, I always thought I did better in groups, when in fact I do better with people one-to-one — which was a key strength of which I wasn’t even aware.  Some of these things are just hard to see.

My advice on this front is three-fold:

  • Be aware of your strengths and beware your natural tendency to overplay to them.  If one of your strengths has become a running joke (e.g., at one point one of my staff handed out “Captain Anal” pins), it could be time to think about it.
  • Be aware of your weaknesses and, while you can work on them if you want, use building a complementary team as your primary way to compensate.
  • Attend programs like LDP (managers, directors) or LAP (C-levels) to build a deep understanding of both.  These programs aren’t cheap, but they will give you self-awareness, in a kind of data-driven and ergo virtually undeniable way, that few other programs will.

(And can somebody please spell-check this thing to make sure there aren’t any errors.)