I recently sat down with the legendary sales leader, Adam Aarons, for a fireside chat with my community of founders, Highland. And wow – did he bring the fire. 

If you don’t know Adam, he’s been the Chief Revenue Officer (CRO) for three incredible tech companies – two out of three (that I know of) have scaled beyond $100M+. 

1. Okta
2. Classy
3. Drata 

Okta became a public company, and as of this writing is worth ~$15 billion. And yes, the second company was the one I founded and was acquired by GoFundMe in 2022. Several years prior to that, Adam became our first-ever CRO and helped us truly professionalize and scale our 100-ish person inside-sales organization. 

At the time, we had grown too fast and had become inefficient and bloated. Adam had the un-envyable job of figuring out how to turn our floundering sales team into a well oiled machine again. And he did exactly that. 

We chatted for nearly two hours on this call, so I can’t cover all of the gems (signup for Highland if you want a front row seat next time). But I still wanted to write about a few of the key takeaways that are highly applicable for any founder or CEO that’s trying to figure out how to scale sales. But this isn’t, “get more leads”, “increase your win rate”, type of advice. These are three non-obvious lessons that I personally learned from Adam and was happy that he shared with the Highland community too… and now you as well!

Let’s dive in… 

1. Never lose late 

This was one of the most valuable lessons that Adam ever taught me as a leader And, it’s applicable to any process where you are trying to get someone to do something you want: 

• Buy a product
• Renew a contract
• Partner with you
• Invest in your company
• Buy your company 

Basically it boils down to this. The worst and most costly mistake any sales person can make is to wait until the very end of the process, only to learn that you lost the deal. Why? Because you spent all of your time and energy losing, not winning. The sunk cost here is massive and adds up across all lost deals. And, as it turns out, you were highly unlikely to win the deal in the first place. The signs were there, you just chose not to see them. 

This doesn’t mean you throw in the towel on every deal that has a bumpy patch. It means creating repeatable systems to screen out bad prospects. To create an early warning system across the sales team that says: if a prospect does X, Y or Z in respective stage A, B or C, then we walk away and reach out again when the time is right. This takes the guess work out of it and empowers reps to walk away and spend their energy on the more probable deals. 

Adam shared a powerful analogy about great white sharks that captures this philosophy perfectly: 

“Off San Francisco Bay, great whites expend enormous energy hunting seals. If they hit too many surfboards instead of seals, they’ll die. Sales opportunities are the same – you need to know if it’s a seal or a surfboard early, because you can’t afford to waste energy on the wrong targets.”

Yup.

Scot’s take

We’ve all been there. A prospect is acting shifty. Avoiding our calls. Making excuses. Yet, they say they’re still interested. They just need a little more info. A little more time. A slightly larger discount.

And, we really need the money. So we hang in there. We hope it’ll work out in the end. Finger’s crossed!  But then we lose. They were talking to a competitor that we didn’t even know existed. They were just looking around and were never serious buyers in the first place. Their budget was never going to align with our sales price. And so on and so forth.

Adam taught me to avoid chasing the losers and start selling the winners. Don’t treat each prospect equality. Find the prospects that are most likely to close, as early in the sales process as possible, and give them your all. Then walk away early from the ones that are low probability. Just never lose late! 

2. Optimize CEO-CRO Relationship

The relationship between the CEO and the head of sales is one of the most critical partnerships in any scaling company. As Adam says: 

“When you hire someone to do this job, look for someone that can take the ball and run with it.”

Someone that doesn’t need constant approval and oversight from the CEO. Someone that can help the CEO instill a winning mindset across not just the sales org, but the entire company. 

Here’s what Adam believes makes this crucial relationship successful: 

1. Trust Must Be Mutual: At Classy, when Adam needed to reset revenue targets during a particularly challenging board situation, it required immense trust between the two of us. As he puts it: “Let the sales leader tell you what the numbers are gonna be. Don’t tell your sales leader what the numbers have to be.” Call your shot and hit it, even in downtimes.
   
2. Embrace Productive Tension: “I told Scott, ‘You live in a bubble. You hired me to pop your bubble.'” A CRO should be willing to challenge the CEO’s assumptions and bring ground truth to strategic discussions. “People will bullshit you because you’re the CEO. They won’t tell you your baby’s ugly. I always will.”
   
3. Clear Responsibilities & Alignment: The CEO needs to remove obstacles and provide air cover, while the CRO needs to own the revenue strategy and execution. When these lines blur, problems arise. This doesn’t mean the CEO can’t help sell certain deals under the guidance of the CRO. But it does mean the CEO can’t operate by one set of rules, while the entire sales org operates by another. 

Scot’s take

t’s typical for founder & CEO to be the first, and often, the best sales person across the company. And the transition from founder-led-sales to a legitimate sales organization is often a tough one to make. It goes from largely gut feel, to building a repeatable and measurable sales process with many moving parts. It took me too long to realize that I needed someone like Adam (a head of sales in general) and that I couldn’t do it all myself. 

Looking back, I would have started building the sales organization even earlier and hired a head of sales to lead it. I could then act as a part time “sales rep” working the largest deals alongside the head of sales. That way the head of sales could learn my tactics and implement the best ones across the team. This skill transfer is key. Afterall, why wouldn’t every new sales rep want to adopt at least some of the founder’s tactics (as long as they are working!). Then, the head of sales can start to analyze each step of the sales process from a math perspective. And they can lead the charge to optimize each stage for conversion, ultimately driving up the over-all win-rate across the floor. 

3. Mission vs. Performance: A False Choice

One of my favorite moments in our conversation came when discussing how to balance a mission-driven culture with high performance. This was especially relevant at Classy, a software company that served nonprofits. Naturally we attracted a very mission-centered team. And sometimes the juxtaposition between sales culture and impact culture was challenging to manage. 

As Adam said: 

“When I first got to Classy, people told me that they were here for the mission — not revenue”

But that didn’t make sense to him. The relationship between mission and revenue isn’t either/or. 

“We needed to synergize the two. We care about revenue because if we do well, we can serve so many more companies and serve our mission so much better.”

This isn’t just lip service, it’s actually true. So how do you raise the bar on performance in a mission-centered culture? Here’s what Adam said: 

1. Clear expectations: “We have a very specific sales process that we hold an expectation for. Everybody’s bought into it, or they can’t be here.” This line is drawn right up front.
   
2. Team First: Everyone is expected to do their part. We pick each other up when needed. “We don’t hire mercenaries. We’re a team – high tides float all boats.”
   
3. Hard Convos: You don’t sugar coat stuff just to make everyone feel good. “Being a member of the sales organization is like a marriage. If it’s not working, you act and you act quickly.”
   
4. Shared accountability: “Everyone needs to understand how they contribute to both financial and mission success.” Once they do, they are accountable to those results as part of the team. 

Scot’s take

In the early days, Classy had a “family-like” culture. Extremely mission and product centric. Less so, sales-centric. But I knew we needed to mature if we wanted to become successful (and lasting) in the market. So I hired leaders like Adam to help push the culture forward in the right direction. 

Sometimes the “old guard” will take issue with these cultural evolutions. They’re comfortable with the way it’s always been. And rightfully so, they have great pride in what the original team has been able to accomplish. But what got you here won’t get you there. Change is necessary for growth. And a big part of this change is increased levels of accountability across the team, and at the individual level. You can’t build a high performance team at scale without high levels of accountability. 

But in mission-centered cultures there tends to be an imbalance between passion and performance. Call it 3 parts passion, 1 part performance. This is fantastic on the passion side. Most companies would kill for this amount of personal motivation to exist between its four “walls”. But passion can’t supersede performance. Passion should fuel great performance. And this is the type of culture that Adam helped me build, and any great sales leader can help you with too.