Twilio Regional Vice President, Retail Sales • December 4
So much of the sales KPI tracking has been automated (# meetings, Pipeline generated, funnel progression) so I find the manual ones more difficult to track, but move the needle the most. ie: how many on-sites did a rep conduct this quarter? It's a manual process for reps to log into a CRM and update a meeting field as "in person" and often gets over looked in an organization. There is no substitute for in person meetings. Another example that's difficult to track things like how many new business units or contacts from other business units you broke into in a month, quarter, or year.
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HubSpot Senior Director of Sales | Midmarket • December 17
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.
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HubSpot GTM Leader | Building Products that help Sales teams win | Formerly Clari, CallidusCloud (SAP), Selectica CPQ, Cacheflow • November 12
Communicating value effectively isn't about having the perfect pitch. It's about having a system that enables you to drive credibility, identify real pain, and maintain momentum throughout the journey. Here are the core considerations to include in your system: 1. Establish credibility – Be someone worth listening to, early on. This means coming prepared, demonstrating expertise, and speaking their language. Credibility is earned by showing you understand their industry, challenges, and the outcomes they care about. 2. Identify & implicate pain – Discover the problem beneath the surface and highlight its impact. This is about asking the right questions to uncover hidden issues and then framing those problems in a way that connects emotionally with stakeholders. 3. Reference relevant use cases – Show them they’re not alone, and that others have succeeded with you. Share stories of similar organizations that faced similar challenges, and how your solution helped them achieve tangible results. 4. Map pain to value – Demonstrate clearly how your solution addresses their specific challenges. Create a direct line from the pain points identified to the value your solution provides, making it obvious why your approach is the best fit. 5. Sell a thoughtful evaluation plan – Guide stakeholders through a process where everyone knows their part and what’s next. A well-structured evaluation plan helps build confidence and ensures that all decision-makers are aligned on the steps to move forward. 6. Align on investment – Ensure they agree: this is a problem worth solving with time, energy, and budget. Make sure each stakeholder understands the cost of inaction, and that solving this problem is a priority worth their investment. 7. Establish ROI – Use value engineering to build an ROI model that lives across a worst case, most likely, and best case threshold. This will help quantify the value and show different possible outcomes, making it easier for the committee to see the financial impact of your solution. 8. Push professionally – Keep everyone focused and committed to moving forward, even when things get busy. Be respectful but assertive, maintaining momentum by setting clear expectations, follow-up actions, and deadlines. When selling to an executive committee, it's important to understand where the power lies in the organization and pressure-test your champion on their ability to wrangle team members to test your value story. The dynamics of a larger committee often mean multiple perspectives, varying priorities, and different levels of influence. Navigating this effectively requires knowing who holds decision-making power and ensuring that your champion has the influence to bring others along. Each time you're meeting with new decision-makers, you're running through the above system or process. You'll need to start a new mini sales cycle all over again. The objective is to align everyone who has power to get a deal done to your desired outcome, which, of course, will align perfectly with your champion's desired outcome. Value selling is an ongoing commitment. It’s not about pushing product—it's about helping others realize what's possible when real problems get solved.
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Carta Senior Director of Sales - Venture Capital at Carta • December 10
The most important intangible traits for account executives include a strong willingness to learn, grit, and the ability to build meaningful relationships while earning clients' trust. They should position themselves as thought leaders in their industry and be genuinely passionate about what they sell, as this authenticity drives success. On the tactical side, organization is the most critical skill. Account executives who manage their book of business with structure, clarity, and a sense of ownership—treating it as if it were their own company—are far more likely to be successful.
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Iterable VP, Growth Sales, B2B2C Sales & LATAM • April 16
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?
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Fastly Senior Director, Global Sales Enablement • September 10
Great question. I will frame my answer with what I see is the biggest transition most sales organizations are looking to make in today's economic climate - trying to move away from 'vendor-like sales' to a more 'consultative / trusted advisor' sales organization. Where i see the most vital ingredients to do that include the following: To be successful in sales going forward, professionals need a blend of both hard and soft skills to navigate the evolving landscape. Here are the most important ones: Soft Skills 1. Emotional Intelligence (EQ): The ability to understand and manage your emotions and the emotions of others is crucial for building relationships and trust with customers. Additionally, show up constantly with a perspective to your calls (you don't really care about the weather! Talk about trends you are reading about in their industry instead) and be authentic in your curiosity (every time you talk to some one its an opportunity to do discovery). 2. Active Listening: Listening to customers’ needs and challenges, and truly understanding their pain points, is key to offering relevant solutions. Also, be sure to multi-thread and learn from more than just one 'champion' - build the army of those who can do the selling for you when you're not in the room! 3. Adaptability: The market, products, and customer needs change rapidly. Being flexible and open to learning helps you stay ahead. Get out to industry events, read blogs, do some research in order to stay on top of what's happening....it shows you care 4. Become a Maser Storyteller: Clear, concise & persuasive customer stories helps in delivering compelling value propositions and negotiating deals effectively. 5. Relationship-Building: Cultivating strong, genuine relationships with clients helps in driving long-term business and trust. This will lead to more business over the duration of the account. Deals take time....don't just show up for when customers initially sign on the line that is dotted - show them you are there for the long term and that your focus doesnt open happen when you see potential dollar signs Hard Skills 1. Sales Methodologies: Mastering value selling frameworks like MEDDIC, Sandler, or Challenger allows professionals to follow a structured and repeatable process for closing deals. This is the future of sales - the days of 'feature function selling' are dwindling - you need to earn the right of customers time and wallet share by demonstrating value 2. Data Analysis: The ability to interpret sales data and analytics can help professionals identify trends, improve strategies, and make data-driven decisions. It can also lead to a repeatable and scalable sales play for others to follow 3. Digital Literacy: Understanding and leveraging digital tools, from automation to social selling, can help sales teams work more efficiently and engage with customers across platforms. 4. Product & Customer Success Knowledge: Deep understanding of your own products, services and how your customers are being wildly successful with them is critical to articulating value to your potential customers and aligning your solution with their needs. Together, these skills and approaches equip sales professionals to meet changing customer expectations and succeed in an increasingly digital sales environment.
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Asana GM, AI Studio • December 5
I think any KPI that is not integrated into the quota and comp structure for any AE by and large is misguided. If you want AEs to focus on specific behaviors then build it into their comp plan and prioritize quota relief over increased commission payments if you have to choose. There are only two exceptions to this in my mind: any KPIs (pipe coverage, onsite meetings, etc.) where you can establish a direct connection to the health of those metrics and their ability to close more revenue OR behavior changes you might want to see mid year, in which case you can use SPIFFs as a tool to align incentives to the behavior changes you want to see. And for any behaviors where the KPIs or SPIFFs are not baked into their quota, be sure to have dashboards that accurately reflect what is happening and commit to communicating regularly progress each AE is making against them. They will otherwise be lost or forgotten about as quota relief and commission always reigns supreme.
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Zendesk Director, Commercial Sales - West • November 14
Good OKRs define the output you are looking to achieve. Be clear in your outcome and give your sellers the space to define their process. Your managers can lean in on process suggestions, if they need help there. It can be easy to focus on effort metrics like volume of calls or emails, however if the true goal is simply the weekly PipeGen that was achieved or amount of revenue that was booked, use them as your North Star. For roles where they also act as Post-Sales/Success, instead of monitoring meetings, you may want to hold the team accountable to product activation, usage milestones, or active users.
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Outreach Sr Director of Strategic and Enterprise Sales • December 18
Great question — I would recommend a few principles here for setting KPIs into new markets: * Start small: understand what the 2-3 wins will be over the first few months into this new effort. Let’s set KPIs in accordance with those wins, and communicate them clearly to the team, and to the executives supporting that new endeavor. * Report on them early and often: stay close to the KPIs in a new market endeavor—it’ll help identify trends to early wins and opportunities for adjusting KPIs. * Retain the right to get smarter: You need buy in from the team that we’re starting with these KPIs, but we will get smarter and will edit those as we go along. If you have an enterprising team, they’ll want to provide feedback and you’ll want to hear it from them, and adjust course.
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HubSpot Director Sales DACH • November 19
Everyone should own the KPIs which are relevant to achieving the goals. If you can't influence the KPI they become less relevant and impactful. The context of the KPIs are also important if the intent is to drive behaviour. If there is no attention from management to KPIs this is probably also a good indication that they are no longer a priority.
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