I really like this question because it's so true! Leadership can break a lot of trust by implementing incorrect KPIs for a segment. Experienced sellers will get angry they are treated like SDRs, etc. The best thing leaders can do is watch, listen, observe, and then replicate. What have the most successful reps done in this position? Are they having 10 calls a week, 2 on-sites a month, and 1 "high value activity" a quarter (like exec intro, hackathon, etc)? Standardize from the top and make excellence the norm.

I think finding ways to give yourself an edge is always in your best interest. You want to avoid creating too much work for yourself, but there are needle-moving ways to get this edge that don't require a massive lift. If you're in a role play interview, treat it like a real sales process. Send a pre-call email with the agenda and goal of the call outlined and send a follow up email in the format you typically would in an active deal. Prepare thoughtful and custom questions to ask each of your interviewers that show how you think, what you care about, and your business acumen and/or natural curiosity.

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.

With most of these questions, there isn't a one size fits all. Consider things like: * Company stage * Growth objectives * GTM strategy * Customer segmentation * Self serve vs. sales led * Compensation modeling AI has, of course, been a hot topic lately, begging the question of which roles will become obsolete. Personally, I think there will always need to be a human element. This AMA is a great example. If you wanted these answers you could find a generic response in Chat GPT vs. reading my response, but you are looking for the human experience aspect that ideally will provide you with more value. Below is a brief rundown of how I'd think through my org structure coming in at an earlier stage business. It's less about the actual title of the role and more about the function itself: * Inbound vs. outbound * Marketing * SDR * Partner/Channel * Customer acquisition * AEs * Customer retention * Onboarding Specialists * Customer Success/Account Management * Customer expansion * AE * Customer Success/Account Management * Customer reporting * Revenue Operations * Customer value * Sales Engineers * Solution Consultants * Leadership * Revenue * Sales * Customer Success * Revenue Operations Are all of these roles needed to get started? No. Figure out where you can create overlap in your roles by working backward on your bottoms up modeling for your revenue targets and determine how many people to need in order to achieve those goals. From here, you can uplevel the structuring into categories: * Functional: Think specialists vs. generalists. Core vs. overlay * Geographic: Location specific * Market Based: Industry/vertical specific * Product Sales: For larger organizations, this can be based on product SKU, bundle, etc. to drive certain revenue engines of the business

When stepping into the role of Head of Sales at a startup that hasn't previously had a dedicated sales function, it's crucial to establish a strong foundation while driving rapid growth. Here's how to approach your first 30/60/90 day goals: First 30 Days: Building Foundation 1. Understand the Business: * Gain a deep understanding of the startup's product or service, target market, value proposition, and competitive landscape. 2. Assess Current Situation: * Evaluate existing sales processes (if any) and identify areas for improvement or gaps in the sales strategy. 3. Define Sales Strategy: * Develop a clear sales strategy aligned with the company's overall goals and objectives. * Determine target customer segments, pricing models, and go-to-market strategies. 4. Build Sales Infrastructure: * Set up essential sales infrastructure, including CRM software, sales enablement tools, and reporting mechanisms. 5. Hire Core Team Members: * Begin recruiting key sales team members, such as sales managers or account executives, to help execute the sales strategy. Next 30 Days (60 Days Total): Growth and Execution 6. Refine Sales Processes: * Streamline and optimise sales processes to increase efficiency and effectiveness. * Implement standardised workflows, sales scripts, and objection handling techniques. 7. Train and Onboard Team: * Provide comprehensive training and onboarding for new sales team members to ensure they are equipped with the skills and knowledge they need to succeed. 8. Start Generating Revenue: * Focus on generating initial revenue by closing deals and acquiring new customers. * Identify quick-win opportunities and prioritize efforts to drive early sales wins. 9. Establish Metrics and Reporting: * Define key performance indicators (KPIs) and establish systems for tracking and reporting on sales metrics. * Monitor progress closely and make adjustments as needed to stay on track towards goals. Next 30 Days (90 Days Total): Scaling and Optimisation 10. Scale Sales Operations: * Scale up sales operations by expanding the sales team, refining processes, and investing in additional resources as needed. * Explore opportunities for geographic expansion or new market segments to accelerate growth. 11. Customer Feedback and Iteration: * Gather feedback from early customers to understand their needs, pain points, and satisfaction with the product or service. * Use insights to iterate on the sales strategy, messaging, and product offerings to better align with customer needs. 12. Establish Sales Culture: * Foster a culture of accountability, collaboration, and continuous improvement within the sales team. * Lead by example and reinforce core values that drive success in sales and customer relationships.

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?

Over-indexing on trying to look good by manipulating the narrative or masking challenges or flaws. Better to be honest and proactive where there are challenges, especially if it is you that has not done well enough to deliver against what is needed. Radical candor is/was talked about a lot but no matter how much practice you get the reality is it is hardest to deliver the truth when it is often most important to do so. My very first forecast call with a new CRO I was nearly certain would cost me my job. Instead, I think in part because of my honesty and directness (the news I was delivering was not good!) it turned into a pretty pivotal moment for me and my team as a result.

Very interesting question — and one that brings up a few more! * Quota attainment is a KPI that is directly meaningful to a seller—if she can hit her KPI of quota attainment year after year, that will be meaningful to her personally! * However, quota attainment isn’t a helpful KPI to the company by itself — we could find out that the above seller is selling bad deals — selling deals that have low margins, high churn rates, and more… This is why it’s important to have a several KPIs that are developed to the needs of the business—and to the needs of the seller. Otherwise, it’s like judging someone’s safe driving ability solely by whether or not they drive the speed limit. Many people drive the speed limit, but are looking at their phone, or are ignoring their turn signals, etc. It’s one KPI that will help inform whether a driver is safe, but it’s not the only way of determining whether a driver is safe.

Re-evaluating KPIs on a regular basis is a healthy practice for your company. Just because it worked this year, doesn't mean those same motions will work next. For instance, in year's past, you may have been okay working with a Business Head to justify budget. Nowadays, CFO's are scrutinizing expenses more than ever, expecting to see the R in ROI. If you are not involving them early, your success rate is likely suffering. You'll want to evaluate the attributes making up your wins vs the deals you lose, before determining what to use moving forward. It could be access to power, Executive alignment, departments involved, breadth of solution to differentiate from competition, on-sites delivered, problems you're solving, or length of sales cycle. Identify your trends and set those as your targets. Then make sure you have a simply process to track the data and hold your sellers accountable.

Small spaces. The best way to get exposure to your C-Suite is to find where they are and create reasons to be there. This is a common sales practice. That is, do your homework. Figure out where you can cross-paths with your C-Suite and use an opportunity to broker an introduction if one hasn't already been made. Depending on the personality of the person you're trying to get in front of, you should be trying to learn 1 or all of the following things. 1. Do they have an open-door policy? 2. Do they have an Administrator they might introduce you to who can facilitate getting time with the Exec.? 3. What motivates them as it pertains to the business? How are they wired when it comes to where they feel like they are most impactful (Not all executives are going to lean into the same things; if your CEO is a previous sales guy/gal, appeal to that sentiment, the same is true if they are/were an engineer. This is hard in a truly remote environment. If you are trying to broker time with the C-Suite in a truly remote environment, figure out who is close to the C-Suite and run through the same questions above and get sponsorship. Have someone with influence or authority angle you into getting some time with the C-Suite execs. you're looking to get with.