This is such a great question! Having been a sales professional since 2013, I completely understand how burnout can arise, especially with the constant "reset" every quarter. What’s helped me is creating clear personal boundaries with work and sticking to a structured, repeatable process. By focusing on the things I can control and holding myself accountable to weekly, monthly, and quarterly KPIs, I’ve built a more predictable and manageable workflow. I view sales as running my own business—it requires exceptional time management and operational efficiency.

Leverage Simon Sinek's "Golden Circle" to understand the WHY, then align your enablement to the HOW and the WHAT. To ensure your efforts are aligned to the overall goals and objectives, start with some informational interviews with sales leaders gain more insight on they WHY behind the goals. Why = Understand the sales organization’s strategic objectives. Have a clear understanding as to why we are working toward these goals. How = Collaborate with sales leadership to define clear goals for enablement. What are the actions sellers will need to take to accomplish these goals. This can include the specific steps in a process, sales tools or product information, etc. as well as skills needed to successfully reach the goal. What = Ensure your enablement initiatives build the skills and simplify the processes in the HOW that will directly contribute to the company's WHY. Keep in mind that sellers do best when understanding the reasoning behind the goal and will lean into the enablement if you're aligning the HOW and WHAT to the WHY.

Sales leaders can set KPIs around behaviors we want to see and hold the team accountable to them but top performers will disregard them if they don’t find it is what puts them in the best position to achieve their growth targets. That’s why it’s really important to spend meaningful time with your top account executives upfront to be sure you have a pulse on the ways in which they are translating the strategy you’ve set into actual work in the field. If I believe based on the data that it will take five customer on-sites per qtr to drive expansion then I want to be sure my top performers also see that as the benchmark, are consistently driving towards that mark and that they have scalable methods for doing that. Not only does this increase the confidence I can have in the target I set but I can also now enable and inspire the rest of the team to do the same because I’m using a top performer to drive belief and show them how it’s done. Absent this important context, you run the risk of setting unattainable targets, or worse, targets AEs drive towards only because they’re being asked to, not because it actually drives the behavior and results you know lead to the ultimate growth targets every sales leader is out to achieve.

The best sales candidates often share key traits and skills that set them apart. Here’s what top-performing candidates tend to have in common: 1. Resilience & Grit – Sales can be tough with frequent rejections, and top candidates demonstrate the ability to persevere. 2. Emotional Intelligence – They understand customer needs, handle objections tactfully, and build strong relationships. 3. Curiosity & Learning Agility – They are eager to learn about products, industries, and customer pain points, and they stay updated on trends. 4. Results-Oriented Mindset – The best salespeople are focused on meeting and exceeding targets, and they can demonstrate past success. 5. Strong Communication Skills – They articulate value clearly and are persuasive in both verbal and written communication. 6. Problem-Solving Ability – They don’t just sell a product; they offer solutions that address customer challenges. 7. Self-Motivation & Ownership – They are proactive and take ownership of their pipelines without needing constant supervision. These traits help sales candidates excel, adapt to changes, and consistently deliver results.

Hitting the number is the first thing - But this wasn't all that easy to do over these last few years, so here are some things that will provide value to the C-Suite as a sales leader. 1. Keeping the troops aligned to the big picture -- Keeping the team engaged, happy, and focused on the big picture is exhausting but rewarding. C-Suite will pick up an unrelenting positive outlook and will reward sales leaders when applicable 2. Organizing feedback loops from the field to the C-Suite. The C-Suite is always looking for something insanely positive to share with the Board. If you can create feedback loops on things that are working well in the field, create a system that captures and shares it across the business. Slack is great for this. Bring key stake holders in a channel where you share Win Anecdotes about your sales team. I had a channel called #baller-emails. It was just a channel of killer emails my reps sent to customers and their super-positive responses. My CEO ate it up because he would share customer responses with the BoD 3. Continue to find areas of the business that can be optimized/organized. This can be tricky if you are stepping on others' territories -- but if you see there is a solution to a problem or process that, when asked, the process owner says "We do it that way because that's how we've always done it" then lean in and see if you can share a solution. If you're stonewalled at the operational level, find a sponsor in the business who is aligned on making the fix, build yourself a short SMART goal around it, and see if you can make a measurable impact. Record the work, record the results and get a read on if the impact/change was enough to get the interest of the C-Suite. If so, share in the right setting. Take the thank you, don't ask for more. Over time, more problems will need fixing and you might be the person who is asked to "run to the fire" thats where the money usually is.

KPIs can be over-hyped when they solely focus on action and lack direction. E.g. “make 100 dials” can result in sellers sacrificing quality for quantity, or in the case of a company I’ve spoken with — hundreds of AEs calling a now-defunct local pizza line to pad their stats. (True story!) More helpful is to direct the action towards an end that benefits the seller and the business — “make 100 dials or key personas in our database to accomplish this relevant CTA”.

Good question. I have seen these people in my time as a leader as well. However, not all sellers fall in to this bucket, so KPIs should be in place to support the rest of the team and encourage consistent behaviors. I have seen sellers that are more junior in their sales career or new to a business ask for KPIs (reflective of the top sales performers within the team) so that they can add more structure to their day/week and help them formulate a plan that will eventually get them to a positive quota outcome.

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.

A mentor taught me to evaluate opportunities leveraging the VIP framework . The framework incorporates three inputs Vision, Impact and People. Here is a quick breakdown of how I have thought through each of the inputs. 1) Vision: How excited are you about the companies vision and mission? How aligned is the leadership team and company around the vision? Does the company have aspirations of being a generational company solving a large problem set? 2) Impact: Is there an outsized opportunity to drive impact for customers, the company and the people I work with by leveraging my experiences and skillsets? 3) People: Do the folks I'll be working with share similar core values? What is the quality of the leadership team and personnel? What can learn and develop from their experiences?

Our top reps excel at spotting potential opportunities. Since we're focused on run-rate tactical deals in the form of additional license, new initiatives, and pilots, our main stakeholders are typically at the VP level or below. The key here is mastering the art of tailoring conversations - distinguishing between "above the line" and "below the line" discussions ensures that our messaging aligns with the audience. In larger enterprises, industry trends and company direction are often widely available. It's crucial to delve into these trends, gaining a deep understanding of industry challenges and directions. This forms the basis for crafting a unique perspective that resonates not only with the business but also its key players. Once everyone's on the same page and the problem is crystal clear, we can then propose a forward-thinking solution that drives them towards their desired outcomes. What sets this approach apart is its emphasis on discovery. Rather than leading with a product pitch, we invest time in understanding the company's priorities. This makes our interactions much more aligned with the client's needs, creating a more genuine and less "sales-y" experience. This method ensures that our solutions aren't just one-size-fits-all, but tailored to fit the precise needs of each client we engage with.