I’m a high school and college dropout. I’ve also started two successful companies and currently serve as co-founder and CEO of AdStage, a platform that connects marketers to their data across paid search and social, web analytics, and custom business metrics.
Above all, I’m a salesman.
I’ve always been selling. In elementary school, my family moved to São Paulo, Brazil. I knew I needed to make new friends. I also knew the Pokémon craze hadn’t made it there from the states yet. So I started a Pokémon trading card ring, and before long, I had two bouncers and all the best cards.
I understood how to get the better end of a deal — a skill I still have today. Part of sales is positioning yourself for a good outcome, whether you’re trading Pokémon cards on the playground or selling an analytics platform to digital marketers that lets them gain insight into campaign performance.
A few months ago, my company was at a crossroads. Our head of sales stepped away from the company, leaving me with two choices: Hire a replacement or tackle the role myself.
To position ourselves for a good outcome, I chose to lead the sales team. Here’s what I learned.
1) Improving Sales Conversations
An exceptional salesperson has great conversations. When you think about having an interesting dinner with someone, it’s usually because the conversation flowed well. I believe a confident and persuasive pitch is no different. It’s all about finding and maintaining the right cadence. I needed my sales team to take the same approach to conversations with prospects.
Whether you’re a CEO or simply hold a sales leadership position, it’s important to coach your reps on having great conversations with their prospects. Immediately after joining the team, I scheduled a bunch of sales calls for myself and sat in on many as well.
I knew we could do better. I dissected what we were doing and took time to work with each of our reps on the human aspect of a sale, not simply on how to close business. Getting a deal done is a byproduct of a great conversation with an appropriate value exchange (i.e., software for money).
I also wrote a new fleet of scripts and a sales deck everyone started learning from scratch. We saw an immediate change in our calls. Prospects became excited about what we were selling because we were excited about what we were selling.
We were having great conversations born out of newfound confidence, which brings me to my next point.
2) Gaining Confidence
To be successful in sales, you have to be confident in what you’re selling. That was something our team was missing. There’s the good, the bad, and the ugly in every product. Our sales team was caught up on the ugly, and that showed up in every demo.
When I joined the team, my priority was to raise our confidence. I started by getting rid of the ugly — shuttering products that had been weighing us down for years.
As CEO, I was uniquely positioned to advocate to our management team and make this call. If you’re a sales leader, but not the CEO, there are several ways you can lobby your point of view.
First, share a presentation with decision makers and outline the “why” and “how” behind adjusting your processes or product line. Second, mentor and train your reps to focus on the best parts of your product. This decreases your surface area for failure or misalignment with prospects.
Third, be confident in expressing your opinions and educating others. And finally, make sure you have the data to back up your points. Don’t take the easy route of critiquing without any suggested solutions.
When we eliminated the “ugly,” we were left with a product we were proud to sell. Not only did our confidence skyrocket, but we could justify raising our prices substantially.
3) Getting Visibility into the Business
As CEO, it’s easy to lose track of the daily inner workings of your business. When I joined the sales team, I had to learn how to use our CRM. I learned how contracts worked at a billing level. Hell, I even learned how to put together a contract the right way.
Having this level of clarity into the company uncovered inefficiencies that needed to be addressed. It also taught me how to position our company better when speaking to potential investors or board members.
Leading sales calls every day gives me insight and feedback from our prospects and clients. That’s something I hadn’t been getting from the occasional testimonial or new deal announcement sliding down Slack.
4) Saving Money
The good thing about a CEO running the sales team is that they’ll do anything (legal and positive) to ensure the company’s success. And, usually, they won’t put themselves on the comp plan.
If we had hired a new head of sales, we would have paid their salary in addition to paying out their bonus structure. As CEO, I accepted the role without adjusting my pay or taking commission on deals I close.
These are the decisions that make your board happy and show investors you’re willing to do whatever it takes to make your company lean and healthy.
There will be a day when it’s no longer the smart or economical decision for me to remain as head of sales. However, we’re not there yet, and the learning opportunity is too large to pass up.
1) Adapting to Change
It was important for me to be adaptable when I joined the team. I needed to walk the line of shaking things up and doubling down on what was already working. That was tough for me to get a handle on.
For example, our previous head of sales had implemented a set of really strong processes. As we were making massive changes to our product and how we sold that product, it was easy to want to throw out some of those processes — even when they were working.
For example, we had a great commission plan that was serving the team well. My initial reaction was that we needed to implement a new plan to accompany our new approach to selling. In reality, the compensation plan was working just fine, and our time and resources were better spent elsewhere.
It was a lesson to me that I needed to adapt to successful existing sales processes like our reps were adapting to my new sales strategy.
2) Knowing When to Hold Back
Similarly, as a CEO, I tend to want to impose my ideas on other people. A huge challenge for me — and one that I’m better because of — was knowing when to assert my opinion and when to yield or activate others to solve the problem.
When I composed and implemented our new scripts, I was really into the details of each call track. But it was important that our sales team put their own spin on the scripts.
That was a moment where I had to pause and make sure I was promoting individuality while keeping the way we talk about the product cohesive.
3) Managing My Time
In addition to leading our sales team, I maintain the normal duties of a CEO at a high-growth startup. It’s hard to balance those responsibilities, but I think most salespeople are hyper-competitive and thrive off a good challenge.
Some days it’s difficult to assess the personalities and career goals of my direct sales reports and those in different departments and prep for a meeting with potential investors or partners.
On those days, it would be easy for me to have someone else log the deal I just closed. As CEO, those are liberties I could take. But I’ve been careful not to cross that line.
It’s important to lead by example. The rest of the team notices how I handle my workload, so I make it a priority not to cut corners. For me, nothing beats hard work.
I’ve noticed when I’m excited about the day-to-day of our company, so is everyone else. Leading the sales team as CEO allows me to share that enthusiasm with my team and the company.
Taking over sales also gave me a renewed obsession with the business. There were so many places where I wondered, “Why weren’t we doing this earlier?” This wasn’t a knock on the team before me. It was a revelation that, “We can be doing even better.”
It’s not without its challenges, but at AdStage, being the CEO and head of sales has truly enabled us to provide a best-in-class product and customer experience.