Lesson 4: Don't Make These VP of Sales Blunders Like I Did


VP of Sales mistakes can kill your opportunity for scale if they don’t get fixed. If you have been following my journey at PatientPop, you know we’ve been fortunate to have a strong first four years, growing from $0 to $40M in recurring revenue in that short time period.

While that’s all fine and dandy on the surface, behind the scenes I’ve made tons of mistakes. Some of those mistakes were easy fixes, while others set the business back a month or even a quarter!

It’s a tough pill to swallow, but making mistakes is part of the game. My goal now is to avoid crucial mistakes, while fixing smaller mistakes I make, quickly.

If you are looking to scale your business as a strong sales leader, I want to share the top 5 VP of Sales mistakes that I’ve made over the past four years, and what I’ve learned by fixing them.

My hope is that you can avoid these blunders in your business by learning from mine!

Hiring Optimizers Instead of Builders

When you’re building out different business units early on (Sales Dev, Closers, Channel, Enablement, etc.) it’s enticing to look around a find someone with that coveted “Director of..” title. That should indicate that the person is a builder, right?

Well…not so fast. It’s imperative that when you add a Director to your team, that you understand the difference between a great optimizer (someone who takes what is already in place and makes it better), and someone that has built programs from scratch. They are two entirely different skillsets.

The former is best hired into a business that has crisp process, great data, and a fully built-out support and sales operations team. The latter is what most fast-growing startups need. They thrive in laying the foundation by measuring the data, iterating, optimizing and repeating. That is WAY different than having great 1:1’s and coaching managers.

Make sure that during your hiring phase, you’re actively looking for scenarios like the one I described above. Reference checks on this are a must. I’d also highly advocate having them walk the Executive team through how they will build their program. It’s an hour of everyone’s time that is incredibly well spent.

Feeding Reps Too Much

Have you ever greatly increased the amount of revenue at the top of a sales reps funnel, only to see marginal improvement at the bottom?

One of the worst assumptions I made early on in my career was that I could achieve double the production from an AE by increasing their pipeline 2x. Right sometimes. Wrong many times.

I’ve found there is a very direct correlation between the number of open opportunities in a rep’s pipeline,and their conversion percentage. For us, once we pass the 40 opportunity mark, close rates plummet.

The decision to double support pipeline while simultaneously doubling quota is famous for coming from finance. On a spreadsheet, it all makes sense. 2x in the top, 2x out the bottom! In the real world, finance doesn’t consider demo prep time, actual demonstration time, opportunity follow-up, etc. That is something that only the VP of Sales understands and can talk to.

Early on, focus on understanding the maximum opportunities someone can carry without seeing a decrease in win rate and anchor to that for your sales development support model. You’ll have highly productive, busy account executives, that are closing at their highest level.

Not Investing in Enablement Early

If you joined my team at PatientPop between 2015-2017, you likely received one week of ad hoc training from several different sales leaders, got plopped down into a desk, and started trying to figure out your job. Not easy. We had a high failure rate and knew we needed a sales trainer. So we hired one.

It was an awesome move. After a month on the job, our trainer had decreased ramp time by a month and ramp performance improved 30%. Our employee NPS score in sales skyrocketed to 65.52% which is considered world-class!

BUT. I still wasn’t running a true sales enablement program.

When you do Sales Enablement right, your Manager/Director of Enablement becomes the cross-functional liaison between sales and other relevant departments. It becomes a closed-loop program that operates in the following order:

  1. Onboarding salespeople

  2. Training salespeople

  3. Advanced training during ramp

  4. Receiving feedback from salespeople and their managers

  5. Applying that feedback to optimize #1-#3

  6. Sharing that feedback to inform marketing

  7. Using that feedback to inform product

If you can create that circular motion I’m describing above, you’ll see improvement in your sales outcomes, but you’ll also see improvement in marketing conversions and deployment of products that your customers have an appetite for. 

Miss Career Pathing

When we received our most recent employee NPS scores, mentioned above, our People team aggregated all of the most commonly used themes in both positive and negative feedback. The most common theme in the positive feedback from my sales team was opportunity for growth/career pathing.

It wasn’t always this way, however. One of the earliest VP of Sales mistakes I made was not setting up career pathing. At best, career pathing in the early stages of our business was ad hoc, and unclear. It caused a great deal of confusion and jealousy, as people didn’t understand why certain reps were being promoted.

Even if it’s v1 of how reps will move through your organization, you should create this as early as possible. In the beginning, it doesn’t have to be complicated. Map out how new hires will move through the currently available roles, and attach standard metrics for achievement. As roles get added, update the document and communicate effectively.

I’ve found that it’s really easy to share career pathing during the interview process so that getting promoted is very clear to the person you are hiring. This sounds like a no-brainer, but when everything is moving one-hundred mile an hour around you, it can be really easy to overlook or be something you’ll get to “once everything calms down”. Hint: It never does.

The Biggest Of All The VP Of Sales Mistakes: Planning too late

Earlier in this post, I mentioned that VP of Sales mistakes can kill your opportunity for scale, and this is the number 1 mistake I’ve made in my business. If you avoid any of these 5 VP of Sales mistakes, this is the one.

Listen, I get it. Putting together an operating plan can be really challenging. It’s time-consuming and requires buy-in from your CEO, CFO, CMO and Customer Success leadership.

I also realize that you’ve likely got a million projects on your plate, and the end of the year seems really far away. I can promise you that it comes much more quickly than you’d expect.

When you get to a point where your business is headcount dependent, and you don’t plan early enough, you’re in a BAD place. Hires get jammed through, onboarding gets expedited, people are promoted who shouldn’t be, etc.

I’d recommend that you begin the process of building your company-wide operating plan in early June, with a goal to finalize at the beginning of July. By doing this, you’ve given your teams two full quarters to plan the hiring strategy, sales modeling changes, etc.

If you don’t do this, you’ll find yourself in a position like I was in 2017, planning for 2018 in September and giving our recruiting team an unrealistic goal to shoot for at EOY. With the Holiday Season around the corner, it was nearly impossible to achieve, and we started off 2018 exhausted and understaffed.

In Conclusion

There are a million different VP of Sales mistakes that can hurt your business. The five I’ve listed above are real mistakes that I’ve made in my role. I highly encourage you to reach out to me if you’re making one of the same VP of Sales mistakes that I made. I’m happy to talk you through, in detail, how I solved them.

Remember, you’re going to make mistakes, and you’re going to make a lot of them. You can get ahead by planning early, laying the foundation for career growth, onboarding effectively, hiring builders and communicating routinely.

What VP of Sales mistakes have you made?