From a mental perspective burnout is definitely a real challenge in sales. I answered another question in how to handle burnout, as a career in sales is a marathon not a sprint. From a tactical perspective, one of the biggest frustrations I have experienced as an AE are constant book-of-business (BoB) or territory changes. AE's can really hit their stride when they can consistently work their BoB, and sudden, unexpected changes can be disruptive to productivity and revenue. Building a strong BoB is one of the hardest part of sales, once the foundation is set I like to give things time, watch reps cook and allows the “magic” to happen. *This is of course if the current BoB/Territory alignment is working.

* Commitment to Win/Figure it Out Factor * Total Ownership * Quick Learner The nuances of the role can be learned. Candidates with the above attributes will overcome any potential skill gaps and always find a way to be successful. When interviewing a candidate, I'm always looking for multiple examples of stories where these attributes are showcased.

I like a consistent review of competitive win rates by stage. I think these can serve as early signals to so much: from how your narrative is landing, whether price is where you fall down or perhaps even foresight into late losses building up as a result of a missing piece of functionality or two. We have the benefit of someone who dedicates the majority of their time on content creation, visiting with customers and regular analysis of our results. Whether or not you can make this a full-time job, I think carving it out intentionally for a relevant function to own is worth it - the insight is invaluable.

Let me answer this from the perspective of one of my key cross-functional partners—Product Marketing (PMM). When we first sit down with PMM teams, they usually have a lot of information they think will be helpful for sellers regarding a new product launch or initiative. However, much of it tends to be 'fluff'—nice-to-have details that often overshadow what sellers actually need. I always ask PMM to think like our sales teams and focus on two key questions: 1. "What's in it for the seller?"—Essentially, how can sellers make money? 2. "What's in it for the customer?"—How can sellers use this to make money? If their content doesn't answer these questions, it’s likely just noise. At the end of the day, content creators want their work to be consumed, and helping cross-functional teams understand this sales-focused perspective ensures that everyone wins.

Love this question, too. It's true. There are a few reasons: 1. You will always have outliers in a sales org. Sometimes a rep has a windfall and reaches quota without hitting KPIs, I've seen it. But the point of KPIs is the make success repeatable. 2. It gives your managers a tool kit to help coach and manage performance. 3. How do you eat an entire elephant? One bite at a time. Each KPI is a "bite" and we do best when faced with a big task (annual quota) to break it down to as small of pieces as we can.

To be successful in sales going forward, professionals need a mix of both soft and hard skills. Here are the most important ones to focus on: Soft Skills: 1. Emotional Intelligence (EQ): • Understanding customer emotions, handling objections, and building rapport are critical to gaining trust and maintaining strong relationships. 2. Active Listening: • Listening to what the customer says—and doesn’t say—helps identify their true needs and allows sales reps to tailor solutions effectively. 3. Resilience & Grit: • Sales is full of rejection. The ability to bounce back and maintain a positive attitude in the face of adversity is key to long-term success. 4. Adaptability: • The market, customer demands, and technologies are constantly changing. Sales professionals need to be flexible and able to pivot quickly. 5. Effective Communication: • Clear, concise, and persuasive communication, both written and verbal, is essential to conveying value propositions, closing deals, and maintaining client relationships. 6. Problem-Solving: • Customers are looking for solutions to their pain points. Being able to identify problems and provide tailored solutions separates top performers from the rest. 7. Collaboration & Teamwork: • Sales is increasingly collaborative, requiring coordination with marketing, product teams, and customer success. Building strong internal relationships helps sales professionals deliver better results. Hard Skills: 1. CRM Mastery: • Knowing how to efficiently use Customer Relationship Management (CRM) tools like Freshworks CRM for tracking leads, managing pipelines, and analyzing sales data is critical for sales effectiveness. 2. Data-Driven Decision Making: • Sales teams now rely heavily on data to inform their strategies. Sales professionals must be comfortable interpreting analytics and using data to drive decisions and forecast accurately. 3. Sales Automation & Technology Tools: • Familiarity with sales automation tools, email marketing platforms, and lead-generation software helps streamline workflows and increase efficiency. 4. Product Knowledge: • Deep understanding of the product or service you’re selling is essential. This enables you to articulate its value, answer technical questions, and position it against competitors. 5. Negotiation Skills: • The ability to navigate complex negotiations and find win-win solutions is a crucial skill for closing larger, more complicated deals. 6. Social Selling & Digital Presence: • The ability to use platforms like LinkedIn and other social networks to engage prospects, build personal brands, and generate leads is becoming increasingly important in modern sales. 7. Market & Industry Knowledge: • Understanding the broader industry landscape, competitors, and trends helps sales reps anticipate changes and position their products more effectively. Conclusion: • Soft skills such as emotional intelligence, communication, and resilience will help sales professionals build relationships and navigate challenges. • Hard skills like CRM proficiency, data analysis, and product knowledge ensure they can operate effectively and strategically. Balancing and developing these skills will help sales professionals succeed in an evolving sales environment.

Sales stakeholders can come from any department within an organization and as the company grows, their input is key to sales success. A few examples may be: 1. Product Teams: aligning sales strategies with new offerings and/or customer feedback 2. Marketing: greater integration for cohesive messaging and lead gen 3. Customer success: ensuring client satisfaction and retention 4. External partners: distributors, resellers, support partners can help expand market reach The best method to building and maintaining relationships with your stakeholders is to regularly communicate with them. Show appreciation for their support, inform them of changes, address their concerns and involve them in key decisions that may impact their area of the business. Creating trust and consistent communication will help build, or strengthen, your relationships.

Excellent revenue leaders turn into outstanding revenue leaders based on how and who they hire. Your number one job as a leader is to hire the right people, followed by supporting them. If you only hire A+ talent, your team will only need you for strategy vs. blocking/tackling personnel and process issues. Some things to consider: 1. Define the sales culture: 1. Talent density: Slow down to speed up. We only hire A+ talent. Those who embody the innate skillsets that are difficult to teach (i.e. humility, hustle, high IQ/EQ, curiosity, relentlessness) 1. Create a robust recruitment process to ensure you don’t deviate from top-tier talent. Great books to reference: Who & No Rules Rules 2. Crystal clear on your mission, vision, values, and the importance of maintaining a strong culture especially at the age of our business. 3. What are the skillsets and behaviors of your top performers today? You use the current examples of what you have to help define what sales excellence means to your business. 4. Create revenue incentives to drive the right behavior (i.e. AE & CS comped off expansion so they can work together to drive customer outcomes) 5. Recognize and reward top talent, while also celebrating the struggles and failures in order to learn and grow 2. Define and create a revenue motion: 1. Define clear roles & responsibilities for all revenue 2. Define clear KPIs, both shared and individual 1. Expectation setting on performance/winning culture 2. Performance management. Make tough decisions early and often 3. Create and constantly iterate a revenue playbook in order to drive repeatability in our motion and forecast 4. Leverage data to gain insights into sales performance, customer behavior, patterns of successes/failures, and leverage leading indicators to guide decision making 3. Establish virtuous revenue training: 1. Clearly defined onboarding program to reduce time to ramp. Learn from your previous new hires. Every new hire should help iterate the onboarding playbook for the next round of hires 2. Continuous call reviews to ensure our ICs are following your sales methodology. MEDDPICC can be fairly outdated. I recommend building a model from several methodologies that get your GTM team to understand customer use cases, challenges, desired outcomes, how to solution sell vs. feature sell, key risks within deals, executive alignment, multi-threading, etc. 1. Custom training dependent on findings (i.e. value selling, objection handling, negotiation, competitive positioning, etc.) 3. Foster collaboration, problem solving, sharing best practice 4. Sell 90 initiative: ICs spending 90% of their time with the customer. This means we remove all internal inefficiencies. 1. Technology overhaul: What’s working, what’s not? 4. "We are customer obsessed": 1. Customer-first mindset. Maniacally focused on value selling, understanding pain, providing solutions, and making your customers' lives easier. 2. "We pride ourselves on building long-term relationships" 3. "We don’t put the competition down, we’re trusted advisors and know our competitors gaps inside and out"

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?

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.