It’s Not Your Sales Leader, It’s You: How To Strike Balance in The Founder-Sales Leader Relationship

Most startups begin with founder-led sales. And they should. It doesn’t make sense to hire a sales leader until you’re able to give them the springboard to do what they do best.

However, once a certain level of growth is achieved and you’re ready to fund, build, and scale a growing sales team, it’s time to pass the baton.

It sounds so easy, right?

And yet it’s not a simple transition for many founders to make. Founders—especially technical ones—tend to think linearly about the outcomes. Sales leaders think about all of the twists and turns to get to the outcomes.

It’s like Goldilocks and the quest for the just-right temperature of porridge. When is the right time to hire a sales leader? And as a founder how do you manage the relationship with your sales leader to grow the business, encourage creativity, and foster trust?

Here’s how to get this relationship right.

Why founders want to be involved in sales

It’s a natural inclination—as a founder, it’s up to you to get it up and running. As the face of the company, you’re working countless hours to validate the market while figuring out how to keep customers coming back for more.

However, founders might get caught in the trap of thinking that if you know your business backward and forward, they should be involved.

Why?

A few reasons:

• They’re too close to the business and can’t let go.
• Initial success has inflated their ego.
• They simply don’t know what good sales leadership looks like and the work required to succeed in the role.

Trust and control are rooted in much of this. If you hire a sales leader, but doubt their knowledge, understanding, or are taken aback by their actions—it makes sense for you to want to be more involved.

So, why does a lack of trust happen in the first place? In my experience, it usually boils down to poor communication—either infrequent, ineffective, or both.

Stepping back and let someone else take the reins

Many founders I’ve coached don’t realize how much they’re giving up by continually grinding away at sales.

I recently worked with a founder that’s been doing all the heavy lifting for their enterprise deals and bigger opportunities. The problem was that he was doing this, and:

• leading his startup;
• managing a sales team of 10;
• managing his customer success team.

In fact, the biggest signal that he needed help was he’d have great meetings with a laundry list of action items he refused to delegate or share. It takes a lot of hard work to get a seat at the enterprise table and even more to keep it, but his inability to let go resulted in critical details slipping through cracks. Big deals fell through. He was setting a bad example for the team. And the company suffered from buyer AND staff turnover.

Does this sound familiar? Unfortunately, it can be hard to think clearly about the business when you’re buried in the weeds.

Scale your involvement alongside your company’s growth

James Murphy, VP of Global Sales at Glofox, believes that from Seed to Series A, founders should be involved in all enterprise-level deals.

But any involvement after that can reflect poorly on the company.

“I think once you get past A, and you’re moving into Series B, having a founder on the call makes you look small to some of these bigger companies, and the founders should be close to what’s happening, but not on the call,” he said.

Once you get past Series A, founders should have their focus on the “10,000-foot-view of what’s in the pipeline, what’s moving, and roadblocks.”

A founder’s involvement should scale right along with the growth of the company.

One of the best ways to address this is to step away from the minutiae and see what breaks. Is it something that should be delegated, removed, or hired for?

When you have the right people around you as a founder in the right roles and doing the right work consistently, your business can scale and grow.

Building trust starts with hiring right

Hiring a sales leader before you have a sales process in place is like putting an Olympic swimmer in a swimming pool before it’s filled with water. They can’t do their best work because you haven’t set the environment they need to get the job done.

In fact, a sales leader is someone you want to hire to accelerate pre-existing sales into the upper echelon of success. But they won’t be able to do this if you keep wrestling the reins from them.

So how do you set up a sales leader in your startup to flourish with your trust?

It starts in the hiring process and taking the time up front to understand:

• What good looks like for the role
• Why it’s time to hire now
• Success milestones in the first year
• What happens if the role isn’t filled

Knowing the answers to these questions coupled with a hiring scorecard creates an environment to confirm/deny alignment. No alignment, no retention.

It’s also an opportunity to set the stage for creating expectations early and often together.

Here’s what happens when you hire a sales leader too early

If your startup doesn’t have a steady stream of revenue and you hire a sales VP early on, it may:

Waste precious capital

If your sales VP does not have a seat at the table and you treat them like a glorified sales rep to do your dirty work, it will be the most expensive hire you make.

Consider this: the average base salary of a VP of Sales for a startup begins around $185,000 and can climb to $275,000 when you factor in upside, equity, benefits, perks, bonuses, and more.

The average salesperson’s salary is a fraction of that. So you may be able to save your company a ton of money by getting another salesperson or two before investing in a VP of sales.

Stall the growth of your sales team

A VP of Sales should help bring structure and efficient processes to the table whereas the day-to-day sales grind is better left to your salespeople.

That’s why your expectations for your VP of Sales should be much higher. Without sales, you don’t have a business.

A VP of Sales should be responsible for:

• Working with marketing to understand the best GTM strategy
• Understanding the post-sales buyer journey to pinpoint buyers at the highest risk of churn
• Crafting a plan to address the core issue of missed revenue targets
• Creating a repeatable, measurable, and scalable process to engage the buyer where they are
• Recruiting and hiring the best salespeople to do the right work for your stage
• Helping them scout, engage, and close better deals
• Build, reinforce, and strengthen your culture
• Scaling your sales team for growth

A VP of sales should NOT be responsible for making sales calls. If you hire them to sell and lead a team at the same time instead of strategically growing your business, it’s not going to work out so well.

Keep in mind, just because hiring too early isn’t suggested doesn’t mean you should wait until it’s too late either.

Hiring too late won’t help either

It’s not always a safe bet to wait out hiring a VP of sales for your startup and continue to do the work on your own. In fact, it’s hard to see just how much time it consumes and how many opportunities you leave behind.

Running your sales team will pull you away from crucial aspects of your business, such as innovating, improving, and raising money with the right partners, that only you can do.

So now you’re not only wasting time running sales (when it’s not your forte to begin with), but you’re also letting your product suffer and losing market ground.

Case study: A founder’s failure to hire costs a lot

I spent a lot of time with a founder six months ago. He is leading his sales team with an ineffective “player coach” sales leader, because he is not confident the leader can:

• Develop winning sales strategies for new segments
• Pinpoint pricing, and
• Hire and retain outstanding talent.

The business has stalled, the pipeline is lackluster, and this key hire is frozen because the founder can “get by while they cut expenses to achieve efficient growth.”

Fast forward to today. He’s still grinding away with a flimsy GTM strategy, a costly mishire (he parted ways with the player coach), a frustrated team, and not a lot of pipeline or revenue. How this helps the bottom line for “efficient growth” is beyond my comprehension.

Now you’re probably thinking: “Okay, great. Don’t hire too early or too late, got it. So when will I know the right time?”

The right time to hire a sales leader

These six signs point to the right time to hire a sales leader for your startup:

1. It’s bigger than you. If you’re leading the sales team and notice important details like hiring, onboarding, process, deal management, coaching, and strategy slipping through the cracks, it’s a great signal to bring in a VP of Sales.
2. You know your market and have a well-defined value proposition. If you don’t have this squared away, you’re wasting a lot of money and priceless time hiring someone while making zero headway.
3. You have sales reps in place, repeatable revenue, and a process to back it up. Your VP of Sales should be able to step in, hone and refine the process, embrace hiring and onboarding, and lead the team to realize sustainable, repeatable results.
4. You’re ready to make the investment to scale. Having at least $1M in ARR is a good benchmark to consider when it comes to making significant investments, like hiring a VP of Sales.
5. You’re ready to give your new VP of sales autonomy to build. The number one request on the “must-have” list we receive from VPs in our hiring process is to truly have a seat at the executive table. Founders, you must be comfortable letting go of the reins so this key person can leverage their expertise to strengthen and scale your startup.
6. Your startup is prepared to jump to the next level. This is where perception versus reality is table stakes. Your startup must be in a position to scale. If your VP of sales does their job well, you will be rolling in sales while seeing major growth. Are you ready for the influx?

Look for repeatability within your business today to help you determine the best time to hire your VP of Sales. If you’re relying upon hope versus key business milestones, it’s best to work on your sales team and your process first.

Pro tip: be realistic with where your startup is today and the near future

The lion’s share of founders I speak to that reel from the nasty effects of a mishire are those that hired for the future of the business rather than what they needed at their current stage.

The beauty of hiring a sales leader at the right time is being able to rely on them for the time-consuming parts of the sales process. This is how you get to focus on the big picture and tap into where you can add the most value.

What’s the line between helpful and detrimental involvement?

A founder never really stops selling. They’re the catalyst for recruiting fundraising. Think about how many opportunities come from all of that selling activity.

But there’s a difference between selling the big-picture idea to investors, employees, partners, and closing deals with customers.

It’s all about finding a healthy balance. And nothing is more important than cohesion between the founder and their sales leader.

Setting boundaries together is essential to striking a healthy balance. These boundaries will change as you grow together and as long as you regularly communicate together to set them. Creating a safe environment is crucial so you can be open, honest, and accountable with each other.

If boundaries get crossed by either side, you have clear signals something is off before it gets out of hand and can course correct together quickly.

Remember, tough conversations are part of the game—don’t let this stuff slide! But it starts with releasing control.