In order to get a better understanding of what you could be walking into, I suggest asking the question "What is your biggest problem and can I help solve it?" It shows genuine interest in the interviewer's pains/goals and enables you to see how you can make an impact. Aside from this key question, always make sure to check out these resources before stepping into the interview. 1. Company Website: Familiarize yourself with the company's products or services, mission, values, financials and recent announcements. 2. LinkedIn: Research the hiring manager and other key stakeholders to gain insights into their backgrounds and professional interests. 3. Glassdoor or RepVue: Read reviews from current or former employees to learn about the company culture, interview process, and potential interview questions.

I think there’s a lot to be said about optimizing sales processes with AI. As software continues to improve this will allow AEs to be more productive, manage larger books of business, and deliver highly customized outbound messaging. That said, given the sheer volume of outreach prospects receive today, it’s more important than ever to differentiate yourself, build your network, and establish yourself as a thought leader in your space. If I were an AE starting today, I’d focus on what I want to specialize in and start building relationships—not just with prospects and customers but also with partners in the ecosystem.

As important as any KPI is why the metric is being measured, how you intend to reliably collect and review the data and the frequency you will get together to review the trend good or bad. In entering new markets, however difficult and unpredictable, you need to establish what you do believe to be true: size of the TAM, ICP definition and owners of each stage and target conversion of part of the funnel. Once you commit to the process - and give enough time for the work to show meaningful results, perhaps then can discuss what might feel arbitrary. If after all that there is still uncertainty about what goals might be realistic then commit simply to make improvements each week until there is enough data to set the right goal. Or take a leap of faith, set the goal and over communicate how and why you set it and what you'll do and why if you need to adjust at some point.

Sales leadership in a small company versus a large company involves navigating different challenges, priorities, and dynamics. Here are some key differences: 1. Scope and Scale: * In a small company, the sales team is often smaller, with a narrower focus and limited resources. Sales leaders may be required to wear multiple hats and be directly involved in day-to-day sales activities. * In a large company, the sales team is typically larger, with specialised roles and a broader geographic or market reach. Sales leaders focus more on strategic planning, team management, and driving overall sales performance. 2. Customer Relationships: * In a small company, sales leaders often have more direct contact with customers and play a hands-on role in building relationships, understanding needs, and closing deals. * In a large company, sales leaders may have less direct interaction with customers, as relationships are often managed by account executives or sales representatives. Sales leaders focus more on coaching, mentoring, and supporting the sales team in managing customer relationships effectively. 3. Decision-Making and Flexibility: * In a small company, sales leaders have greater autonomy and flexibility in decision-making, as there are fewer layers of bureaucracy and approval processes. * In a large company, sales leaders may encounter more complex decision-making processes, involving multiple stakeholders, departments, and hierarchies. Sales leaders need to navigate internal politics and collaborate across functions to drive alignment and consensus. 4. Resource Constraints: * In a small company, sales leaders may face resource constraints, such as limited budgets, manpower, and technology infrastructure. Sales leaders need to be resourceful and creative in maximizing the impact of available resources. * In a large company, sales leaders have access to greater resources, including dedicated support teams, advanced technology platforms, and marketing resources. Sales leaders focus more on optimizing resource allocation and leveraging economies of scale to drive efficiency and effectiveness. 5. Risk and Growth Potential: * In a small company, sales leaders may face higher levels of risk and uncertainty, as the company is still establishing its market position and may be more susceptible to market fluctuations or competitive pressures. * In a large company, sales leaders benefit from greater stability and brand recognition, but may face challenges related to market saturation, increased competition, and the need to drive incremental growth in mature markets. Overall, while the fundamental principles of sales leadership remain consistent across small and large companies, the specific challenges, priorities, and dynamics vary significantly based on the size and stage of the organization. Effective sales leaders adapt their approach and strategies accordingly to drive success in their respective environments.

There is a give and take with standardizing KPIs but also having enough variance to account for things segment, (Strat, Ent, MM, Growth) number of accounts, and so on. The easiest way to have consistency and also provide a lens to inspect forecast is by implementing standardization when possible. No matter what segment you're in or how many accounts you have, if a deal is 345 days old... that's going to tell me something about the forecast accuracy of the stage it's in. I am a big fan of ensuring reps are training that in the mid point of the quarter or month, whatever your quota and cadence is, deals with a close date in quarter or in month must be in Best Case, Commit, or Closed. Nothing can be in "Pipeline" or "Omitted"

Consistent benchmarking of reps against the top performers within a sales org. This could help assess coaching needs on a regular basis and also identify any talent gaps that need to be considered when recruiting new reps. The coaching needs maybe be around product based knowledge or fine tuning a reps management of a sales cycle.

While tech may have downsized lately, great sales professionals still have lots of options. The major driver of recent layoffs were to create more efficiencies in businesses; which leads to lower burn and more profitability. There are few roles as efficient and impactful on profitability as a top seller exceeding their quota. By nature these folks will always be sought after and have options - so retaining top talent should always be a priority. The biggest mistake I see in retaining talent, is front-line managers DAM'ing their team. They only manage: D- Deals - when the deals are there and closing life is good! When they're not, the only lever they have is to drive activity. A - Activity - when deals are there, activity check-in's are infrequent and leading indicators of poor future pipe are missed. Once the pipe dries up, poor managers micro-manage activity and ramp up the urgency on activity without offering much actual guidance on how to drive better conversions. "Do more" is the mantra. M - Morale - any decent manager is going to check-in with their team. If they aren't truly helping their AE be successful then morale will probably be good when they're winning, and lower when they're not. Especially low when they're being micro-managed for prospecting... Now let's compare this and understand why a top performer would stay in the first place. There are 4 core reasons and an elusive and fleeting 5th reason. 1. They feel successful, are making money, and feel they're being fairly rewarded for their work. 2. They're developing skills and growing. They know that the hard work they put in today will pay dividends down the road. 3. They see opportunities for career progression and advancement. They believe there is opportunity to get promoted, or take on meaningful work that would represent professional growth, in an acceptable timeframe. 4. They're having fun and/or enjoy the people they work with & for. If you hit all 4 of these and/or if you are a part of a very mission-driven organization with inspirational leadership, you can tap into the 5th category: 5. They feel like they're a part of something bigger than themselves. This last one is a by-product of doing a lot of other things right. But if you can reach that pinnacle - this issue will take care of itself. Now if we apply the DAM method to why people would stay: 1. If the deals are there, the DAM Manager would theoretically focus on and help the AE close their deals. When pipeline is present the DAM method can work. Of course if it's not - this is strike 1. 2. Outside of situational deal coaching, there's no skills development carved out in the DAM method 3. Promotions are a by-product of hitting your number or not 4. It's fun when you're winning and unless you're on a great team, you don't really enjoy where you work when you're in a slump. A normal person needs 3-4 to feel good about where they work, 2 to be okay with it, and 1 to begrudgingly stick around. Literally everything above is dependent on there being enough pipeline and the AE closing deals. There is absolutely no reason for someone to push through to the other side when things get difficult. This is what causes someone to hit the bare minimum of requirements and demand a raise or promotion. They aren't having fun (4), they're not developing skills (2), they aren't making the money they want to make (1), so the only way to justify their existence is to get promoted (3) - which will give them fleeting relief until they move on 6 months later after the other 3 don't change and the next promo is 2 years down the road. So what DO you do: 1. Everything is easier when you're winning. I'm not going to break this down too deep - but more people feeling successful, hitting quota, making money, setting records, the more they'll want to stick around and keep doing it. Also check quotas to ensure they're realistic, attainable and surpassable. Make sure comp is competitive and I'm a big fan of accelerators to ensure your most talented AE's put the hammer down after they've hit quota instead of backing off. You can also get creative and make the highs higher. President's Club produces so many memories and is a silent motivator throughout the year. Hi-Po dinners or events for top performers throughout the year are another worthy investment. Once you've had a taste of being in the exclusive club for top performers you never want to back. 2. Working on Skills Development is where I think most companies can improve their standing with talent. Learning slowed down when we went remote. You used to have to be less intentional, and the osmosis of hearing everyone do the job, or being able to ask your neighbor a question, improved skills naturally. This has dropped off a cliff. According to the Bridge Group, ramp time now sits at 5.7 months compared to 4.3 months in 2020. This is an industry wide problem. While you can (and should) analyze your onboarding program, possibly hire outside training for a shot of adrenaline, and look at your enablement team for help here - it's not all on enablement. The gap is more on day to day coaching. Leaning in and investing in your front line leaders to be better coaches and develop THEIR skills to uplevel the AE's skills is where you'll have the biggest impact in my opinion. The bar for this also gets higher as the AE gets more talented, so it's important that front line leaders can not just coach the basics, but can help talent get to the next level. "Coaching" or "skills development" in general however just doesn't take up much real estate on enough managers' calendars. 3. Upward mobility is another silent motivator that drives people to keep working hard in the background. If your most talented people have reached the highest rung - you should identify this as a risk and think through if there are opportunities to create a new promotion level, carve out more responsibility, or add a rung to the ladder in some way. I've interviewed so many AE's who were talking to me because they felt "they had learned everything they can at their current company." Don't ever let that be the case, or don't be surprised when they leave. One thing I undervalued coming up as a leader was clarity of promotion path. I thought it was obvious that if you performed at an elite level, you would be in the conversation for a promotion. Some people can put their head down and operate at their best under these guidelines, but you miss your core performers. Core performers hate this answer, and by getting more clarity around the exact expectations for a promotion, you can often get more out of these folks as they work towards checking off all the boxes. I have also tried to talk talented people off a ledge who felt like it just wasn't clear how they get to the next level. We need to know that taking a new job, with a new title, at a new salary, is always crystal clear. So if someone is in their office at home, thinking through their next couple of years - if they can't see how they would move up in your organization, it's going to be a lot easaier to believe their easiest path is to go somewhere else. Change this, and prove it. It's so important to show promotions and ensure everyone knows those stories - what they did, how they did it, and how "you too can get those same results." 4. In a remote world "fun" is a lot harder to come by. I used to love coming to the office. My teams typically loved it too. We had a great group of people that genuinely enjoyed working together for the most part. Energy was through the roof. We had tunes going, people on the phone, we celebrated everything, gongs were ringing, jokes were made on the floor, deals were broken out live, people were learning, succeeding and had camaraderie around them to push through it if they weren't. We'd go out together from time to time and we made work fun. That is just near impossible to replicate in a remote world (if you have the secret sauce DM me!). What you can focus on however is building culture. Putting together an intentional team that wants to lean in, engage, and work together in this new capacity. Create opportunities to collaborate, learn and grow together. Anoint members of your team who have a pulse on the rest of the team to step up and help drive this so it lands. They can fill your blindspots. Invest in getting people in office whenever you can. If someone really likes their boss, this can make a huge difference too. Ensure your front line leaders are a big plus in this column. Which leads us to number 5 5. While a lot of things need to click for the team to feel like they're a "part of something bigger than themselves" there's one quality that will keep people around well beyond the point of logic, and help create a dedicated army for the cause. Inspirational leadership. You can find this at all levels - however you've heard about an inspirational leader behind many of the world's most iconic runs. Tesla had Elon Musk. Apple had Steve Jobs. Yammer had David Sachs. Hubspot had Brian Halligan. OpenAI was about to lose the whole company when they tried to oust Sam Altman. People will follow inspirational leadership through hell and come out the otherside unscathed and still committed. It doesn't need to be a silicon valley legend however. There are inspirational managers, directors, VP's and team leads across the industry. I feel this is undervalued however. If talent is really thinking about leaving - are they inspired? Are you inspiring them? If this feels like a gap - start with clarity of the Mission. What hill are we taking, what's our goal - beyond just hitting revenue targets. What's the strategy for hitting that goal? Why does that matter for the team? What's in it for them? Why are they lucky, one of the chosen few, to be on that mission here and now? If you can answer all of those things - people are probably inspired. If not - it mght be a good exercise. I map all of this out in detail to provide the ability to audit your own org, or an individual. You would love to answer yes to all 5, but identifying where the no's are can give you a clear roadmap on what to fix to systematically retain talent. 1. Do they feel successful, are making money, and feel they're being fairly rewarded for their work? 2. Are they developing skills and growing? Do they know that the hard work they put in today will pay dividends down the road? 3. Do they see opportunities for career progression and advancement? Do they believe there is opportunity to get promoted, or take on meaningful work that would represent professional growth, in an acceptable timeframe? 4. Are they having fun and/or enjoy the people they work with & for? 5. Do they feel they're a part of something greater than themselves?

Top performers can distort KPIs that you want to roll across your team. On one hand, sales professionals are able to achieve excellence because they do the right things consistently “We are what we repeatedly do. Excellence, then, is not an act but a habit.”. For a salesperson like this, we will strive to understand how those habits inform their success, and which of those therefore should be transmutable across the team to drive success for others. On the other hand — this is not popular to say - some of your best sellers are simply far more talented. They will not need the same amount of “at bats” that you’re measuring throughout your sales funnel as the sales reps who are a standard deviation or two less talented. Do not build KPIs off of these individuals.

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.

It's best when the collaboration/ideation stage is done as a step towards an outcome, but oftentimes we need to make that pivot from collaborating to leading. Here's what I've found works best: 1. Define Roles & Tasks: Ensure everyone understands their roles & responsibilities. Use the RACI method to start and take into account the team member's skillset, strengths and interests. 2. Set Clear Milestones: Align on deadlines and specific goals that allow each project member to succeed in their role/task. 3. Communicate Expectations: Make sure everyone knows and is in agreement with #1 and #2, then determine how you'll communicate any issues or roadblocks 4. Provide Support: Check in regularly- be a resource and offer assistance, as needed, to hit the milestones.