How My Sales Team Hit Quota Every Month for A Year

As a sales manager at HubSpot, I lead a team of nine reps who sell to small businesses based out of California. Though various curveballs have been thrown our way, we have met or exceeded quota for a year straight, with an average quota of 120 percent month over month.

Like many other sales groups, we have had to be nimble and adjust our working habits to succeed in 2020.

When the impact of COVID-19 picked up in March, we started seeing changes to our sales process. Though we fortunately did not experience significant customer turnover, we were having a difficult time getting prospects into our pipeline. Our team had to focus more on activities at the top of the funnel, qualifying prospects to ensure they were a good fit for our products and had the budget to spend.

Our team also had to swiftly transition to remote work which had its own challenges.

Previously, our entire team worked in the office with the occasional person working from home on one-off occasions and we thrived working together in the office environment. Now that we are all working remotely, the DNA of our team is forever changed.

Yet even with these working changes, we have still been able to meet or exceed our numbers every month. Here’s how we did it.

How My Sales Team Hit Quota for One Year Straight

1. Allow flexibility in the sales process.

We make it a point to be extremely realistic about where we are as a team. Whether we are being open and honest about how we’re feeling that day, or about where we are in our pipeline, transparency is key.

In small business sales at HubSpot, there are two ways to hit quota — you either close fewer high-dollar deals or sell several smaller deals. Some teams consistently aim to sell high-dollar deals and that’s their specialty. Conversely, some teams focus on closing several smaller deals each month.

On my team, our deal sizes can vary from month-to-month because we take a more flexible approach. Within the first 10 days of the month, I check-in with my team to see how their conversations with prospects are going. I ask, "what kind of month is it going to be? What do we need to do to make quota?" Based on the preliminary data reps provide at the beginning of the month, we can plan around those trends and switch gears accordingly.

For example, at the beginning of April, we noticed we were closing smaller deals. Our average sales price was lower than in previous months, and the transactions were trending smaller. After seeing that trend start, our team decided to ramp up activity and focus on closing more deals to make up for the smaller deal size.

Selling to small businesses allows us to switch gears quickly, increasing our sales velocity when needed.

2. Create tailored development plans for reps.

I make tailored coaching plans for each rep based on their performance. I take their individual strengths and areas of opportunity into account and look for ways to give them more support in those areas.

For example, working in small business sales some new reps have a hard time disqualifying leads early in the process. Because HubSpot follows a freemium customer acquisition model, newer reps need practice distinguishing between who can be served through our free offerings, and who would benefit from our paid offerings.

In this scenario, I would work with the rep to help them understand what kind of businesses actually need HubSpot. We would walk through identifying and communicating with prospects who are a good fit for our products and services so we can make mutualistic sales. Our goal is not to sell people things they don’t need. At HubSpot, we sell in an empathetic way, and we do that by focusing on the prospect’s needs being in alignment with what we do.

I develop reps to come back to that guiding principle. This often looks like me listening in on a few sales calls and providing tangible feedback. Anytime I’m observing reps I try to identify two things that are preventing them from reaching their peak performance level, and from there we’ll come up with a plan to address those specific areas.

3. Ease the transition to remote work.

As I mentioned, our team previously worked in the office full-time, and we were in constant communication due to proximity. Transitioning to remote selling, I have had to adjust my leadership style to ensure my team’s success.

I am now a more organized leader and prioritize documentation and information sharing for my team more than I did in the past. I have also become more intentional with how I coach my reps. Now instead of focusing on coaching reps through specific deals, I am more focused on empowering my team to be better at their jobs overall and supporting them as they hone in specific skills. Ultimately, the goal is for them to do their jobs without me.

When we were in the office our team worked very closely together, and the proximity to one another helped us create a tight-knit community. Every task was an opportunity to collaborate. If the team was feeling behind for the month, we would order food, stay late, and work together as a team to build our pipeline and get caught up on any outstanding items as a team.

Now in a remote environment, we have to work a lot harder to keep the energy up. Working late on a virtual call doesn’t have the same impact as working together in person, so we have become more efficient to alleviate the need to have late catch-up sessions. I’m also very cognizant of wanting my team to have a separation between work and home, and don’t want them to feel like they constantly have to be "on".

4. Examine and adjust expectations as needed.

As salespeople, we tend to be very ambitious. While that is a good thing, we still have to be mindful of how we lead and work with others, especially in the current climate. We are not working remotely because we decided to take a remote job, we are working remotely due to factors outside of our control.

It’s a really disheartening time to be a sales rep, and if a rep is working for a manager that is not understanding about that, it could make their job a lot harder. I’ve found leading with empathy has been really helpful for my team.

If your team is struggling right now, using understanding language can make a huge difference. Even a simple "I know we are in a challenging climate and your job is not easy. I’m here to support you" can go a long way.

I also make it a point to acknowledge my team’s effort when we are doing well. I will say, "I know we’re not doing well because this is easy. We’re doing well because you are working hard."

As a leader, I try to be as transparent as possible with my team. We have had months where even I was feeling discouraged, which doesn’t happen often. After hitting quota several months in a row I sensed my team felt pressure to keep things going. When we finally reached this lull, I wanted to relieve that pressure. I sent my team an email acknowledging what we were all feeling, and assuring the team it is ok to miss quota, as we had met and exceeded so many.

My reps responded well to this message letting me know how grateful they were to be on the team and that they appreciated my transparency. Though we did end up making quota that month, our team was ultimately stronger from the clear communication and humility. Setting expectations that are in alignment with our current reality is critical for keeping reps engaged and motivated.

These strategies have helped our team stay on track with our goals while navigating a volatile market. Though there are still many unknowns ahead, we look forward to meeting the challenge.