Since I joined HubSpot in 2007,  I’ve worked for five different managers. Each was a great sales leader who possessed his own approach to managing and leading his team.  

I’ve summarized 10 of the most important lessons I’ve learned from each of these leaders below. I’ve drawn on these lessons as I scaled my own teams from just me to hundreds of salespeople. If you’re in the process of building a sales team, I hope you find these lessons useful as well.

1) Always be positive.

My first sales manager was Dan Tyre, a man renowned for his infectious positivity, as well as his odd and humorous sayings (dubbed “Tyreisms”).

Sales can be a difficult profession. You’re dealing with rejection at every turn, and it’s easy to dwell on your failures and beat yourself up. In my early days, there were plenty of times when I was frustrated. Fortunately, all I had to do was talk to Dan and my spirits would be lifted instantly. One Tyreism Dan used in times like these was “You are Pete Caputa -- you can do anything you want to.”

Dan is 100% positive about everything he does. He refuses to linger on the negatives. This isn’t to say he glosses over problems. He addresses them, and moves on quickly. In all of the years I worked with Dan, I only made him angry once. Instead of pretending I hadn’t screwed up, he took me aside and explained the problem. After I apologized, he merely said, “Okay, let’s move on.” The smile was back on his face, and the incident was over.

Dan is a living, breathing example of how to recover quickly. Another Tyreism he’d use to inspire someone to bounce back: “Some days you eat the big dog, some days the big dog eats you.”  

Salespeople have enough rejection to deal with. From Dan, I learned that a sales manager should radiate positivity and support. Much of selling is attitude, and a positive outlook from the top can bolster a team’s spirits and help them excel. That’s why Dan is often heard saying “Go, [rep's name], go!” In one short sentence, he’s simultaneously celebrating victories with individuals and encouraging them to do it again.

2) Accentuate unique strengths.

Dan also has a great way of empowering his salespeople. Too many sales managers try to impose their personal sales processes on their direct reports. But although a certain method worked for the manager, everyone has unique strengths that might make a radically different approach the best option.

At the beginning of every month, Dan asks his direct reports to write down three things they did really well over the past few weeks and three things they want to improve upon. He picks from the three things they did well to help the rep figure out how to leverage that strength more often. In addition, he helps them work on the improvement area that would have the most impact.

By using simple management processes like these, Dan has become a master at uncovering a rep’s individual strengths and helping them harness those strengths to perform even better. Instead of making his team members ascribe to his philosophy, he cultivates a wide variety of unique sales approaches.

3) Leverage Marketing.

Eventually, I transitioned from direct sales team member to starting our agency partner program. During this period, I worked for our VP of Marketing at the time, Mike Volpe.

Mike’s first suggestion was to conduct webinars for agency professionals. At first, I thought it was a bit odd to have a sales guy doing webinars, but I quickly realized that it was the best way to get prospects to literally raise their hands. I conducted webinars and the interest flew in.

As a sales leader, it’s important to set your sales team up for success. The other day, I sat down with a CEO who was explained that day-long on-site training programs were producing strong sales for them. Meanwhile, they had a list of 40,000 contacts and hadn’t recorded a webinar version of their training yet! After telling my story, he quickly realized he was missing an obvious opportunity to educate thousands of prospects at a time.  

Bottom line: If you’re not leveraging Marketing to drive demand, you’re missing a huge opportunity to maximize your sales team’s success.

4) Have a sales process.

When it was time to start scaling the agency partner program, I began reporting to Mark Roberge, who was at the time HubSpot's VP of Sales. As a team of one, I scaled the partner business fairly quickly, and eventually reached the point where additional reps were needed. Mark agreed that it was time to form a channel sales team, but asked how I planned to train my reps considering that I didn’t have a formal process in place. I dismissed his concern, saying that I would listen in on calls and coach reps from there. “No big deal,” I said.

Everything went smoothly with my first two hires. But then I added four more reps in a two-month period, and my system (or lack thereof) broke down completely. The team was confused and frustrated. At this point, I took Mark’s advice and documented a process. The results spoke for themselves.

Some salespeople can figure out how to sell something new on their own through trial and error. But no manager should expect their reps to simply “figure it out,” especially as a manager’s coaching time gets spread thin as new hires come onboard.

So, before you build a team, have a defined process. Putting a documented process in place makes sales coaching significantly more effective.

5) Don’t hire on gut feeling alone.

Too many leaders hire reps based on their gut alone. From the very earliest days of the company, Mark was insistent that managers base hiring decisions on a list of criteria. Because this approach was built into the DNA of the company, I never hired anyone without a list of criteria in hand.

But It’s also critical to measure the success of manager’s hiring decisions over time. Whenever someone new was hired, Mark would ask the manager to predict the new rep’s likelihood of success. Two years later, he analyzed the data, and found that while we were pretty good at predicting who would be rockstars (the top 25%), the rest of our predictions were often incorrect. To correct the problem, we iterated on our criteria and interview process over the years. 

Hiring is too important to trust to your gut, which often lies to you. If you don’t use criteria in your hiring process, I highly recommend you start. If your sales management team is new to hiring, I'd also recommend implementing an assessment and seeking outside support.

6) Experiment.

How do you know what works and what doesn’t if you don’t try? Mark has always been a proponent of experimentation, which has resulted in some of HubSpot’s most successful programs and processes. But I think the way Mark implemented the experimentation culture within the sales team was especially wise.

Mark would take time to meet with any sales rep or manager who had an idea about improving our sales results. He was an excellent partner in brainstorming and designing structured experiments. Mark occasionally checked in to provide guidance or put up some guardrails, but for the most part he stood back and let the individual do their thing.

The ideas that worked for one rep were later shared with the team. Rather than forcing the entire team to experiment, Mark let the individuals who were passionate about a given project teach the rest of the team or even lead a new team. Because they felt ownership over the idea, they were more committed to implementing it, even as the project hit inevitable road bumps. We successfully introduced a lot of changes and launched a lot of initiatives in this way.

7) Simplicity trumps complexity.

There’s a time for innovation, and there’s a time to scale, and the two don’t always work in conjunction.

After several years of launching different go-to-market experiments within the sales organization, we created a fairly complex structure for a young company. The different teams were governed by different lead ownership rules. As a result, deal-by-deal conflict began cropping up. In addition, some reps and teams felt they had a better chance of hitting targets than others, and this uneven playing field was fostering bad blood.

In order to curb sales team in-fighting, CEO Brian Halligan stepped in to help us streamline the organization. We put in place a set of simple rules that governed who could work what deal when. We also eliminated many of the individual processes that each sales division had instituted, implementing a common sales process which included the best practices from all teams.

With everyone on the same page once more, the team started performing better and more consistently than ever before. From this experience, I learned that simple is usually better than complicated. If account ownership rules and sales processes start to become overly complex, it’s up to the sales leader to take a step back and identify opportunities for simplification.

8) Overcommunicate.

When you’re rolling out massive changes to the entire sales team, you can’t just make one announcement … or even two, or three. Leaders need to communicate changes multiple times in a variety of formats to ensure they reach every corner of the sales floor.

Brian (and Mark) are excellent communicators. Every time a change was made, they made sure that each and every member of the sales team was aware of what was coming down the pike. Remember that the burden of spreading information doesn’t fall on the team members -- it falls on the leader.

9) Challenge your team.

I currently report to Hunter Madeley, SVP of Sales. Hunter hasn’t been at HubSpot too long -- just over a year and a half -- but he’s already made a significant impact.

The first thing Hunter did when he came in was announce to the sales team that the old bar of 100% wasn’t high enough anymore. He reset the bar at 125% of quota, and adjusted incentives accordingly. 

Just asking the team to do more seems like a wishful strategy. And that is, frankly, what I thought at the time. But Hunter told the team he was confident they could achieve better than 100%. We were a team capable of extraordinary results, so he didn’t feel it was right to have us shoot for 100%. That was the moon, and we could reach the stars.

So what happened? More reps hit or exceeded quota than ever before. To me, this demonstrates that leaders shouldn’t be afraid to set the bar high, so long as they provide the support needed to reach audacious goals and a bit more incentive to do so.

10) Always be recruiting.

Another lesson I learned from Hunter is to always be ahead of hiring targets. For example, if you have a hiring target of five reps for the month of June, you should instead strive to bring on six or seven. Why? Getting ahead on hiring is one of the best ways to get ahead on next quarter’s and next year’s targets.

But if you hope to stay one step ahead, you can’t just wait for the best reps to come to you. You have to go out and find them. This means that sales managers must proactively recruit their people. With this in mind, Hunter has pushed sales managers to get involved much earlier in the recruiting process by reaching out to more candidates more proactively.

These are just a few of the lessons about sales leadership that I’ve picked up from my managers over the years. If I’ve learned anything from my time working with these great leaders,  it’s that there’s no one “right” way to lead. Leaders need to pick and choose the management elements that work best given the challenges and opportunities in front of them. Hopefully, these stories of great leaders inspire you to lead a bit better as you scale your own organization.  

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Originally published Oct 9, 2015 7:00:00 AM, updated February 01 2017


Sales Leadership