Brian Bresee

If I were a sales rep trying to justify a raise, I would ensure I know: -Performance against quota -Percent to goal -MRR / ARR sold -If at a very early stage company, your contribution to the company's growth might be material, what % growth on the top line did you drive? -If larger, I'd be thinking about the KPI impact of strategic projects. I.e. if you developed a sales play that increased close rates of your peers from 20 to 30% - can you quantify that impact in revenue. It's a lot easier to ask for a raise when you can spell out that you drove $1 mil in incremental growth above and beyond your quota.

Burnout is a huge challenge for many sales professionals. Many folks in sales burn the candle at both ends - stacking meetings back to back with no break, working 12 hour+ days, and never truly taking a break or signing off. Over time this adds up, and you can get into a pretty demotivated state of burnout as a result. Healthy habits are the solution. There's a company called PeopleFuel that runs a seminar called The Energy Project, that I found incredibly helpful. The thesis is this - you only have so much energy - and things that happen in your day will take away from that energy. Once you hit your 30s, typically demands on your time increase and the energy you have decreases slowly over time. The people that are most resilient to burnout are those that have very healthy habits. The Energy Project breaks this down into Physical, Emotional, Mental, and Spiritual. Physical - do you eat healthy? Do you get regular sleep? Do you exercise regularly. Emotional - Are you self aware to how you feel? Practicing mindfulness / breathwork / meditation all are really powerful for this Mental - The average human probably has 90 minutes of focus in one go. Micro-breaks are essential to "reset" that focus. Can you build in a walk, a quick breather outside, or 10 deep breaths to refocus. Take vacations and fully disconnect. Spiritual - do you have a deep connection to purpose? This could be religion for some folks, charity, or just understanding the purpose in their work and how it fulfills them. TLDR: Even with a monthly quota (and i've had over 160 months of them) sales is a marathon not a sprint. If you take care of yourself with healthy habits, you are wildly more resilient to the stresses of sales quota.

There are two primary paths for sales professionals who want to continue to level up in sales. The individual contributor path and the management path. Individual contributors might start as an Sales Development Rep or Business Development Rep. These are entry level sales roles that involve appointment setting for a more senior Account Executive who then takes a meeting and works to close business. At most tech companies, the most junior Account Executives work in the small business division, and more senior reps sell to progressively larger segments. So career progression might look like BDR -> Small Business Account Executive -> Mid Market Account Executive -> Enterprise Account Executive On the other side, if you pursue the management track, you may promote in any segment from account executive to manager. Typically this involves taking on leadership responsibilities (something like a team lead program to get experience) and coaching peers to development the management skillset. This could look like BDR-> Account Executive -> Sales Manager -> Director -> VP of Sales.

Sales can be a rollercoaster. You and your company are always judging your performance by what you've done lately. Missing quota is impossible not to take personally, and it's inevitable. Dealing with the highs and lows of selling month in and month out can be super difficult, it's very important to build a healthy process for handling stress and live with healthy habits or it can get the better of you.

The best sales leaders have a few things in common: -They have a deep mastery of how to sell effectively -They are incredible coaches and development focused with their team -They care a LOT about their people Why these three things? First, I've often heard the refrain that "you don't want to hire the number 1 sales rep to be a manager." That said, no one wants to follow a sales leader who isn't incredible at sales. Imagine if you had a new manager promoted over you, and their average attainment was 60% of goal. How would you feel about working for them? Not great right? So if you are interested in sales management, I would first learn how to crush your quota and become a top 15% rep. Second, the best managers I've worked with are exceptional coaches. Many new managers struggle with what we call "super-repping," where they have 7 or 8 reps, and they get on every single call and sell for their reps. Sounds great right? You tee up the call and know your manager will knock it down. But this has a hidden cost. A manager can't be everywhere at once, and their team never truly learns how to do it on their own. Coaching and development focused managers spend their time building up the skills of their reps - not to sell exactly like them - but to lean into their own style and develop 1 skill at a time, constantly adjusting the coaching to challenge the rep to push their skills further. As a manager, you have leverage (the ability to dramatically scale your impact beyond yourself) in developing great new sales people, not selling yourself. You don't want to be the hero, you want to build heroes. Third, the best managers I've ever worked with truly care about their team's success over their own. People can tell if you care. You will often make more money as a top rep, so don't become a manager unless you truly want to help build the next top performing sales rep. I once received the advice from a leadership coach that "people will forgive a lot of mistakes if you show you truly care about them" and I find that to be true. They'll also be way more committed, open to your coaching, and willing to invest their emotional energy in winning if you have their back.

I think context, speed, and quality of sales conversation will be essential. Prospects have less patience than ever, they expect you to know them, their industry, and have deep knowledge of everything in your business that might solve their problems. People expect lightning fast response rates - if I have to wait on hold for 5 minutes I'm hanging up the phone. Sales reps who have a unique perspective that educates and helps the prospect, who respond incredibly fast, and prove that they can listen + are equipped with the systems and information to "stack the deck" so they start with as much context about the prospect as possible will win.

I've been at HubSpot for 14 years. Every year I ask myself the same questions: -Do I enjoy the people I work with? -Am I continuously progressing my career and growing my earnings potential? -Are there new and difficult challenges that stretch me and push me to develop new skills? -Am I fulfilled by the work I do? If all the above are yes, I stay in the role. So far, I've been very fortunate to have a great career at HubSpot. When evaluating new companies, I would recommend a few things for folks to evaluate. First off - life stage and relative risk tolerance can be important to think through. If you are early in your career, have a larger appetite for risk, and are willing to risk a "bad bounce," early stage companies are higher risk / higher reward. If you are later in your career and desire more stability, have family earnings obligations, or just want lower risk in general, later stage companies are the right move. Once you've established stage, I like to think about the intersection of your experience and what you are passionate about. Sit down and write a list of industries / areas that get you excited, then also write where you have experience and knowledge. Often where you overlap is a great place to start. Next, I'd make a target list of companies. Companies that have happy customers (in tech you can see customer reviews at G2crowd, trustradius, or other industry sites,) happy employees (Glassdoor,) and a steady growth rate (look at pace of funding rounds, or read their earnings reports if publicly traded,) are a good bet. I'd suggest solving for growth - mid to high growth companies have many more promotion opportunities and your equity will likely go farther. From there, I'd check linkedin to look for connections in your network that are at one of your target companies. Personally, I'd almost never apply through a job listing, I would always reach out to the connection, ask for 15 minutes to chat about the company, and then ask them to refer you in.

I love to ask a rep to walk me through a deal they closed. Then I ask for a second deal. Then I ask for a third. And I really spend time having a deep conversation on the third. I'm a huge fan of behavioral interview questions (and most hiring analytics suggest they are the only types of interview questions that correlate at all to future job success, which is why you see them so often.) But it also requires skill from the interviewer. The goal of the interviewer is not to sit back and listen to a rep deliver a perfect STAR format behavioral interviewing response, but to really spend time and curiosity learning about the sale. So I might ask about the 3 deals, and on that third deal I want to really explore with questions like: -How did you initially find the deal? -What was your first conversation like? -What problems were they experiencing in their business? -Was there ever a time where things went sideways? What snags did you run into? -How did you negotiate to close the deal? And many more - the idea being if I can understand how they think and sell and what actually happened - I'll have a better handle on their skills as a salesperson. For example, if we are talking through your deal, and I ask about closing, and your response is that you gave a super deep discount to get it across the line, I would suspect there might be a gap in getting to pain or opportunity in your qualification. So I'd want to further explore how you understand pain, build value, and present a point of view that solves for that business problem.