Tag Archives: Startups

How to Manage Your First Sales VP at a Startup

One of the hardest hires — and one of the hardest jobs — is to be the first VP of sales at a startup.  Why?

  • There is no history / experience
  • Nobody knows what works and what doesn’t work
  • The company may not have a well defined strategy so it’s hard to make a go-to-market strategy that maps to it
  • Any strategy you choose is somewhat complex because it needs to leave room for experimentation
  • If things don’t work the strong default tendency is to blame the VP of sales and sales execution, and not strategy or product.  (Your second VP of sales gets to blame product or strategy — but never your first.)

It’s a tough job, no doubt.  But it’s also tough for a founder or new CEO to manage the first sales VP.

  • The people who sign up for this high-risk duty are often cocksure and difficult to manage
  • They tend to dismiss questions with experienced-based answers (i.e., well we did thing X at company Y and it worked) that make everything sound easy.
  • They tend to smokescreen issues with such dismissals in order to give themselves maximum flexibility.
  • Most founders know little about sales; they’ve typically never worked in sales and it’s not taught in (business) school.

I think the best thing a founder can do to manage this is to conceptually separate two things:

  • How well the sales VP implements the sales model agreed to with the CEO and the board.
  • Whether that model works.

For example, if your team agrees that it wants to focus on Defense as its beachhead market, but still opportunistically experiment horizontally, then you might agree with the sales VP to build a model that creates a focused team on Department of Defense (DoD) and covers the rest of the country horizontally with a enterprise/corporate split.  More specifically, you might decide to:

  • Create a team of 3 quota carrying reps (QCRs) selling to the DoD who each have 10+ years experience selling to the DoD, ideally holding top secret clearances, supported by 2 sales consultants (SCs) and 2 business development reps (BDRs) with the entire team located in a Regus office in McLean, VA and everyone living with a one-hour commute of that office.
  • Hire 2 enterprise QCRs, one for the East and one for the West, the former in McLean and the latter in SF, each calling only on $1B+ revenue companies, each supported by 1 local SC, and 2 BDRs, where the BDRs are located at corporate (in SF).  Each enterprise QCR must have 10+ years experience selling software in the company’s category.
  • Hire 2 corporate reps in SF, each sharing 1 SC, and supported by 2 BDRs calling on sub $1B revenue companies.  Each corporate rep must have 5+ years experience selling software in the category.

In addition, you would create specific hiring profiles for each role ideally expressed with perhaps 5-10 must-have and 3-5 nice-to-have criteria.

Two key questions:

  • Do we know if this is going to work?  No, of course not.  It’s a startup.  We have no customers, data, or history.  We’ve taken our best guess based on understanding the market and the customers.  But we can’t possibly know if this is going to work.
  • Can we tell if the sales VP is executing it?  Yes.  And you can hold him/her accountable for so doing.  That’s the point.

At far too many startups, the problem is not decomposed in this manner, the specifics are not spelled out, and here’s what happens instead.  The sales VP says:

The plan?  Yes, let me tell you the plan.  I’m going to put boots down in several NFL cities, real sales athletes mind you, the best.  People I’ve worked with who made $500K, $750K, or even $1M in commissions back at Siebel or Salesforce or Oracle.  The best.  We’re going to support those athletes with the best SCs we can find, and we’re going to create an inside sales and SDR team that is bar none, world-class.  We’re going to set standard quotas and ramps and knock this sonofabitch out of the park.  I’ve done this before, I’m matching the patterns, trust me, this is going to be great.

Translation:  we’re going to hire somewhere between 4 and 8 salespeople who I have worked with in the past and who were successful in other companies regardless of whether they have expertise in our space, the skills required in our space, are located where out strategy indicates they should be.  Oh, and since I know a great pharma rep, we’re going to make pharma a territory  and even though he moved to Denver after living in New Jersey, we’ll just fly him out when we need to.  Oh, and the SDRs, I know a great one in Boise and one in Austin.  Yes, and the inside reps, Joe, Joey, Joey-The-Hacksaw was a killer back in the day and even though he’s always on his bass boat and living in Michigan now, we’re going to hire him even though technically speaking our inside reps are supposed to be in SF.

This, as they say in England, is a “dog’s breakfast” of  a sales model.  And when it doesn’t work — and the question is when, not if — what has the company learned?  Precisely and absolutely zero.

If you’re a true optimist, you might say we’ve learned that a bunch of random decisions to hire old cronies scattered across the country with no regard for strategy, models, or hiring profiles, doesn’t work.  But wait a minute — you knew that already; you didn’t need to spend $10M in VC to find out.  (See my post, If We Can’t Have Repeatable Success Can We At Least Have Repeatable Failure?)

By making the model clear — and quite specific as in my example above — you can not only flush out any disagreements in advance, but you can also hold the sales VP accountable for building the model they say they are going to build.  With a squishy model, as my other example shows, you can never actually know because it’s so vague you can’t tell.

This approach actually benefits both sides

  • The CEO benefits because he/she doesn’t get pushed around into agreeing to a vague model that he/she doesn’t understand.  By focusing on specifics the CEO gets to think through the proposed model and decide whether he/she likes it.
  • The Sales VP benefits as well.  While he/she loses some flexibility because hiring can’t be totally opportunistic, on the flip side, if the Sales VP implements the agreed-to model and it doesn’t work, he/she is not totally alone and to blame.  It’s “we failed,” not “you failed.”  Which might lead to a second chance for the sales VP to implement a new model.

Book Review:  From Impossible to Inevitable

This post reviews Aaron Ross and Jason Lemkin’s new book, From Impossible to Inevitable, which is being launched at the SaaStr Conference this week.  The book is a sequel of sorts to Ross’s first book, Predictable Revenue, published in 2011, and which was loaded with great ideas about how to build out your sales machine.

From Impossible to Inevitable is built around what they call The Seven Ingredients of Hypergrowth:

  1. Nail a niche, which is about defining your focus and ensuring you are ready to grow. (Or, as some say “nail it, then scale it.)  Far too many companies try to scale it without first nailing it, and that typically results in frustration and wasted capital.
  2. Create predictable pipeline, which about “seeds” (using existing successful customers), “nets” (classical inbound marketing programs), and “spears” (targeted outbound prospecting) campaigns to create the opportunities sales needs to drive growth.
  3. Make sales scalable, which argues convincingly that specialization is the key to scalable sales. Separate these four functions into discrete jobs:  inbound lead handing, outbound prospecting, selling (i.e., closing new business), and post-sales roles (e.g., customer success manager).  In this section they include a nice headcount analysis of a typical 100-person SaaS company.
  4. Double your deal size, which discusses your customer mix and how to build a balanced business built off a run-rate business of average deals topped up with a lumpier enterprise business of larger deals, along with specific tactics for increasing deal sizes.
  5. Do the time, which provides a nice reality check on just how long it takes to create a $100M ARR SaaS company (e.g., in a great case, 8 years, and often longer), along with the wise expectations management that somewhere along the way you’ll encounter a “Year of Hell.”
  6. Embrace employee ownership, which reminds founders and executives that employees are “renting, not owning, their jobs” and how to treat them accordingly so they can act more like owners than renters.
  7. Define your destiny, which concludes the book with thoughts for employees on how to take responsibility for managing their careers and maximizing the opportunities in front of them.

The book is chock full of practice advice and real-world stories.  What it’s not is theoretical.  If Crossing the Chasm offered a new way of thinking about product lifecycle strategy that earned it a place on the top shelf of the strategy bookcase, From Impossible to Inevitable is a cookbook that you keep in the middle of the kitchen prep table, with Post-It’s sticking out the pages and oil stains on the cover.  This is not a book that offers one big idea with a handful of chapters on how to apply it.  It’s a book full of recipes and tactics for how to improve each piece of your go-to-market machine.

This book — like Predictable Revenue, The Lean Startup, Zero to One, and SalesHood — belongs on your startup executive’s bookshelf.  Read it!  And keep up with Jason’s and Aaron’s great tweetstreams and the awesome SaaStr blog.