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.

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.

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.

Quarterly and annual OKR's on an individual level need to be broken down from the Company/Segment/Team Level. Once the overall priorities are defined you can identify the contribution on the individual level. I would say to define projects based on the gaps you are seeing and cascade them down to the individual level. Ultimately, the sales goal will be defined by the revenue goal broken down by segment and product. The expected growth rate will determine the priorities. Will the growth come from productivity increase per rep or by headcount growth? Do you have a Total addressable market (TAM) constraint? If yes, how can you increase that? Once those types of questions are answered the goal will be to monitor progress based on KPIs. Most importantly, Revenue, Pipeline and Activities (the order matters!) If Revenue and pipeline is in good order activities become less of an issue. If not, activities need to be looked at to build enough pipeline to reach revenue targets!

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.

KPIs are best socialized in the largest setting, where they are relevant for all stakeholders. This establishes transparency and consistency for those who it applies to. For smaller companies this might be a Sales All Hands, while larger organizations might be done in a Team Meeting. Of course, you'll want to allow for questions and clarity to be proven. This can be done in either a group setting, but I also suggest you give space in a 1:1 for nuanced questions to be addressed. Every seller should be crystal clear on what their goals are and how they are being measured. Once your measurement period is up, whether that be monthly, quarterly, semi-annually, or annually, it is important to reflect with your seller on their specific performance and how it compared to expectations. Speak about what they did to exceed expectations (have them share best practices with their colleagues) as well as what got in their ways from achieving expectations (coaching opportunity on removing obstacles). KPIs should not be a secret and how sellers are performing against them should be very transparent. Do your sellers a favor and don't sugar coat the performance. Clear is Kind.

If a prospect is dragging this out, the most important aspect is getting to understand why... * Did their priorities change? * Is the underlying business case not compelling enough? * Are they not convinced of your solution, so they are buying time to consider competitors? * Do they intend to move forward but internal circumstances have just pushed out the timeline? * Have they decided not to move forward, but don't want to hurt your feelings? * Something else? Regardless of the situation, you need to find out why because Yes's are great, No's are good, but Maybe's will kill you. Therefore, I would suggest having a direct conversation with your prospect. You can do that by... 1. Start with the Why: re-summarize the underlying business case narrative by sharing your understanding in their own of words of the Why: 1) why the prospect needs to do anything, 2) why they need to do it now, and 3) why your solution is the best for their situation 2. Objective Observation: share the objective observation that it seems like the deal has stalled, agreed timelines are slipping, or the prospect hasn't met your mutually agreed commitment, etc. 3. Curiosity: explain to the client it is okay if things have not gone according to plan, but in order to be the best partner to them you need to understand why, and then lead with curiosity to understand what may be going on 4. Way Forward: collaborate to align on the best way forward in partnership with your prospect...it needs to be mutual. Then allow that "Way Forward" to direct what you do next, whether that is marking Close/Lost, circling back when timing is better, or proceeding the sales process with a new found energy.

Top sales reps are often distinguished by a few key intangibles that go beyond just technical sales skills or product knowledge. These traits help them consistently outperform their peers: 1. Relentless Drive – The best salespeople have a deep, internal motivation to achieve their goals. They go above and beyond, making extra calls, following up diligently, and seeking every opportunity to close a deal. 2. Empathy – They truly understand their customers’ needs, concerns, and pain points. This enables them to position solutions more effectively, building trust and long-term relationships. 3. Adaptability – Markets, products, and customer needs evolve quickly, and top reps are able to pivot and adjust their approach without missing a beat. 4. Proactive Problem-Solving – They anticipate potential obstacles or objections and come prepared with creative solutions, turning challenges into opportunities to showcase value. 5. Extreme Ownership – High performers take full responsibility for their outcomes. They don’t blame external factors for missed targets; instead, they focus on what they can control and work to improve. 6. Curiosity – Top reps are always learning—whether it’s about their product, industry trends, or the unique challenges of each customer. This curiosity leads to better conversations and deeper insights. 7. Resilience & Optimism – Sales is full of rejection, but top reps handle it with a positive outlook. They bounce back quickly and don’t let setbacks affect their long-term performance. These intangibles set top performers apart by allowing them to consistently exceed expectations and deliver value, even in challenging circumstances.

Better Together - Collaboration with other departments and Sales Enablement If you have not already started to build out councils with your core heads of department this will allow for set times for you all to meet to collaborate on the enablement priorities and build out RACIs to outline who is responsible during each phase of each project. Below are three steps that can help you start one 1. Meet with all the key department heads that you need to collaborate with to effectively manage or funnel all the information that is required for sales enablement to build strategy and enablement for the field. Explain what your organization is responsible for and how you can partner together 2. Schedule regular cadence with one representative from each group and form your sales enablement governance council - this allows each head of the department to delegate someone to represent that group in any or all projects that require you all to work together. 3. Keep it documented, share the successes, take input and build together The above is the most efficient to build credibility, trust and collaboration with your department heads, remember they will be talking to the sales leaders in other meetings just like you so building your collaboration and trust will help you all partner better together for the benefit of the sales and the organization.

To effectively define the metrics for which you should hold sales accountable, I look at a few things: 1. Understand the "Sales Math" of the business across some core universally applicable SaaS Sales metrics 2. Compare the performance of the top 1/3 AE's against the bottom 1/3 AE's and look for which metrics contribute the most to high performance. 3. Go deep in those categories and correlate the activities top performers do differently to achieve these results. Quantify these activities to define supporting metrics which will lead to success. To break this down, let's understand the foundational "Sales Math." This is the equation to hit quota. The equation is fairly simple, but everyone's vernacular is different. It is actually extremely important to have very well defined steps in the equation to get consistency across your entire team. For example, we use opportunity stages with clear exit criteria for the buyer & seller to provide consistent insight into our Sales Math. So I would actually use a Stage 1 Opp Created - instead of Discovery Call, and Stage 3 Opp instead of Demo. For the purposes of this article, I'll use general sales terms that each business should be able to use as a starting point and customize from there. Here are the metrics that go into the Sales Math equation: * Activities to create a Discovery Call * # Discovery Calls per quarter * # Demos per quarter * Discovery Call to Demo conversion ratio * # Closed Won Deals per quarter * Demo to Closed Won conversion ratio * Average Deal Size * Average Deal Cycle These metrics will allow you to create the math to hit quota. If the current team's metrics do not consistently lead to the results you're looking for, then the Sales Math may be aspirational. If your team is executing against plan, then this may be your actual current metrics. Regardless, this is what you should feel confident telling AE's is the realistic, attainable and surpassable way to hit quota. For example, it could look like: $250k Quarterly Quota Average Deal Size of $84k 3 Deals to hit quota Close ratio of 33% 9 Demos needed per quarter 60% conversion ratio of Disco to Demo 15 Discovery Calls needed per quarter 50 Activities to create a Disco 750 Activities needed per quarter* *one note on activity. It's a metric I'll always track to understand a baseline level of effort, but I will often leave this out of the Sales Math when dealing with higher complexity sales and more senior AE's. Up to you if this should be in your Sales Math equation. Now take your Sales Math, and map your high performers against your low performers to look for which metrics have a high correlation with success. This exercise can be extremely surprising, so be open to what the data shows you, and hold your strong opinions loosely. Let's extrapolate this exercise across two different scenarios: Scenario 1 - Enterprise Here's how the exercise played out when running it against a more enterprise business (numbers are directional): 1. Activity, Discovery Calls and Demos were almost identical across high & low performers. This told me that pushing "more activity" was only going to have so much impact on performance. 2. The Closed Won conversion of top performers was 46% vs. 25% for the low performers. This was a huge gap, and had major implications on the Sales Math. 3. The Average Deal Size of top performers was $160k vs. $70k for low performers. This is also a huge gap compounded the success or struggles of each group when combined with the stat above. So the key metrics to optimize were Average Deal Size and Demo to Close Ratio. We wanted to maintain our activity levels, but really lean into increasing ADS and strategies to help with Deal Execution. Based on this knowledge of what would have the biggest impact in high performance vs. low performance, we added in some metrics & activities that would contribute to these results: * Updated our account prioritization to ensure a focus on the top deals & tracked activity against Priority 1 accounts * We blocked off time each week to prospect into our top accounts & scheduled strategy sessions to help get more meetings with these accounts * We tracked # of Discos with P1 accounts * # of Demo's with $100k+ Opportunities For Deal Execution * We tracked multi-threading in each account * Have we made an executive connection? * We created a cross-functional meeting to lean into competitive differentiation strategy * We set a threshold for accounts that needed a key deal review & updated our process to improve efficiency and make room for more accounts reviewed each week. Scenario 2 - Transactional Here's how the exercise played out when running it against a more transactional business (numbers are directional): 1. There were two camps of high performers. Those with extremely high activity, and those with higher disco to demo efficiency. Our most consistent top performer was a combination of both. Low performers fell into a similar pattern of either low activity or low conversion of discos to demos. 2. Deal size and win rate didn't have dramatic differences outside of 1 AE who closed the largest deal in segment history. This wasn't repeatable so we eliminated that result instead of putting too much time in hunting whales. 3. Average Deal Cycle for top performers was 39 days vs. 52 days for lower performers. Top AE's were closing deals faster, which allowed for more time to close more deals. From this data we defined additional metrics and activities to drive better results: * Upped the baseline activity volume expectations - there is a diminishing point of returns, but higher volume was almost always a component of success. We raised the bar, but also coached our highest volume AE's to lean more into their efficiency metrics instead of pushing to just do more. * Managers went deep on quality of discovery calls coming into the funnel * Title & Seniority level of Prospects - lower conversion was correlated with lower titles. * Was the company in our Ideal Customer Profile? Quality of company greatly impacted conversion * Why now? Did we offer someone a gift card or just bug them until their defense was worn down? Or was this call predicated on funding, a new hire, an inflection point in the business, intent or some other business catalyst? * Managers inspected quality of prospecting messages * Managers inspected quality of discovery calls * We rallied around creative promos to help the team close deals faster * We replicated decks top AE's were using to build value and establish trust faster In both Scenario 1 and 2 - we started with the baseline Sales Math, and through comparison of top performers vs. low performers we were able to lean into the 2 key metrics that had an outsized impact on performance. We then defined key activities and additional metrics which we could hold the team accountable to, that we knew would correlate towards greater success across the team. How easy was that? :)