Last week I told you how I lost millions by not putting profit first at my company, Lemon.io — and how we successfully navigated that crisis.

This week, I’m going to tell you about another mistake that lost me a lot of money. But don’t worry, I’ll also share how we fixed it.

→ Noticing a pattern?

Hit reply and tell me what you think of the newsletter so far. I’d love to hear from you.

–Aleksandr

P.S. — Today’s issue also includes a mind-shifting Q&A with the prolific founder and Chief Revenue Officer, Paul Burani.

We didn’t have a sales team — we had “order takers”

In 2021 and early 2022, staggering amounts of venture capital were pouring into tech startups:

And that was good news for Lemon.io, because…

More funding in tech startups → higher expectations from investors → need for faster product releases → need for more engineers → revenue growth for us:

→ A tech talent marketplace, filled with carefully vetted engineers.

Our GMV grew from $336k in Jan 2021 to $1.5 million in May 2022.

But our growth wasn’t the result of great sales and marketing. It was the result of hugely favorable market conditions.

Don’t get me wrong — we had some wins in marketing, and the sales team was doing a great job. But in times of fast growth, it’s very easy to lose your edge.

And market conditions can quickly change.

A crash was imminent

We were being reckless with spending, not tracking individual campaign performance, and simply chasing the top-line numbers.

Then in March 2022, the VC market went sideways — and so did our growth. To survive, we had to reevaluate everything we were doing.

It’s a pretty frustrating thing for a founder to have to question every decision you made in every aspect of your business: finances, product, marketing, and… 

Sales.

So I turned to my entrepreneur community, Hampton, where I met Wade, an experienced founder who specialized in developing highly-effective sales teams.

And lucky for me, Wade had just sold his last company, so he had some time on his hands. We jumped on some calls where I shared our challenges, and walked him through our sales process.

Wade diagnosed the problem pretty quickly:

Turns out, I didn’t actually have a sales team.

I had a room full of “order takers”.

For years, we had built a solid inbound engine, and our sales team had gotten comfortable — too comfortable. 

“They got spoiled by the infinite flow of leads,” Wade explained to me. “They’re just catching leads all day, and forgot how to actually sell.”

That stung. Hard.

But deep down, I knew he was right.

Even more, we weren’t just bad at selling — we were also bad at working together. Sales, marketing, and customer success were all operating in their own little bubbles. 

• Marketing chased volume, not quality.

• Sales blamed marketing for bad leads.

• Customer success got stuck cleaning up the mess.

• Nobody was actually working together.

This wasn’t just a sales problem. 

We needed to overhaul our entire culture.

I wasn’t confident that I could execute on this — so I offered Wade a Fractional Chief Revenue Officer role, and handed over the keys to the sales department.

Here’s how we fixed it

Wade kicked things off by listening. A lot.

He combed through call recordings, analyzing why some reps were crushing it, while others lagged. He quickly found:

“The best salespeople ask good questions. And then shut up.”

Meanwhile, the rest of the team was just fielding requests, remaining utterly baffled by their dismal close rates.

With that knowledge in tow, Wade implemented a few seemingly small improvements that carried a colossal impact:

It was a huge culture-shift, and took some work to get folks on board — but it worked. 

• We experienced double-digit revenue growth year-over-year.
  

• Conversion rates improved by nearly 30%.
  

• And most importantly, our sales reps started generating opportunities that didn’t come from new leads.

Some reps transitioned into service roles. Some left. But the ones who stayed? 

They actually sell now.

When things are going well, it's easy to assume they always will. 

But if you take the time to build teams and systems that can adapt and thrive, no matter what the market throws your way, you won’t sink when the market dips.

A Q&A with Paul Burani

I tapped Paul Burani, current Founder & Chief Revenue Officer of Mission Flywheel, and former Global Account Lead at Google, to chat about revenue operations, how he could have bolstered his first exit, and more.

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Question 1: Let's go way back to your first business, Clicksharp, a digital marketing agency. You grew it steadily, and sold it in less than three years. If you could go back in time and make one improvement to your revenue operations, what would that be?

PAUL: There was a lot I could have done to run a tighter ship. So much of the business development pipeline was based on networking and thought leadership. I really should have been more diligent about tracking key investments & plotting ROI. 

The financial investments would have been the easy part (membership dues, event fees, sponsored promotion fees, etc.) but more important was the investment of time. 

In a business that is so dependent on referrals, we need to constantly be out there forging new connections and reinforcing existing ones  — but if we don't have an objective view of which efforts are yielding the highest quantity/quality of business opportunities, we cap our upside, and risk burning ourselves out. I flirted with both far too often.

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Question 2: While leading Google's global automotive business line, you achieved 72% revenue growth for Maserati, and delivered Google's "Persuasion & Storytelling" internal sales training. What do those two things share in common?

PAUL: The 72% growth was largely achieved via a YouTube partnership built around using digital video to tell a very unique brand story: this premium brand, steeped in prestige and heritage, was inching slightly downmarket to become more accessible (we're talking $70k entry level prices almost ten years ago, so not exactly mass market). 

The challenge was to convey that accessibility without diluting the brand equity — the kind of dilemma that gives CMOs heartburn and insomnia. 

This was very relevant to the training that I was leading around the same time, where I helped students isolate their own "brand story" and overcome their hesitation in connecting the messenger to the message. 

I find that the best brand marketers make intuitive connections between their audience, their product and ultimately themselves — and we can all learn something about persuasion by watching them in action.

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Question 3: What book changed your life, and why?

PAUL: Right in line with the answer above... Made To Stick by Chip and Dan Heath immediately comes to mind. 

Why? Because we all love it when our own ideas become sticky. It's intoxicating, it feeds our egos, and if we get the details right, it can affect change in the world around us. 

But making ideas stick is predicated on leaving our head space, paying obsessive attention to our audience's head space, and ruthlessly whittling down our idea into a seminal concept that is built for both speed and comfort.

It's one of the hardest things to get right, but this book gives you a very tactical manual for how to do it. It's on a very short list of books I've read where I look back and I can see an obvious difference in my thinking and my work.

Catch you next Sunday! Don’t forget to hit reply and tell me what you think of this newsletter.