Great question and something I love talking to (and sometimes 'debating') our leaders about - the idea behind 'what's the characteristic (or two) of your best seller you would want to clone?' For me, at the top of the list are 2 attributes I look for in potential sales team members: 1) 'Customer first' mindset: I don't want to lead or support a team of 'vendors' who are only interested in selling 'licenses'. I want to enable a team of 'consultants' or 'trusted advisors' that are not interested in selling 'licenses', but providing 'customer solutions' built on value. I want sales teams built on the belief that they can differentiate themselves by showing up to a prospect/customer meeting with curiosity and a perspective on what is happening in the particular industry and company...prospects will pick up on the fact that you seem genuinely interested in understanding their reality. 2) The ability to be a master customer storyteller...something I call 'storyselling'. To me this is an important attribute if you are hoping your sellers show up like 'consultants' and sell on value. Think of how you like to be sold to...most want to partner with someone who understands their current situation, and desired future state. You typically buy from someone you trust, and that trust is typically built out of 'experience' or 'subject matter expertise'. Finally, you want someone who can paint a picture of the future, to get you excited about the 'art of the possible' and nothing means more and comes off as 'authentic' than hearing stories of how other customers, of a similar size and industry, or facing the same challenge, have transformed their business in the way you are looking to do so.

My favorite sales interview question is meant to figure out if a sales rep has really run complex deals regularly. * I ask them to name their top 3 large and complex deals they've closed. * Then I ask them to tell me in more detail about a large & complex deal which is not in the top 3 list they shared. Most sales reps would prepare for an intierview with details about their top 2-3 deals but if a sales rep has truly run multiple complex sales cycles, they should be able to answer this question quite comfortably and in equal detail. The depth of the answer is a good indicator of how well tenured this person is in running complex deals. 

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? :)

This answer is purely based on opinion, so please keep this in mind. I believe that any new tactics and strategies need to be relevant to the sales methodology set by the enablement team. Why? Reps, especially those that are "green" to the field, need a repeatable, consistent skill development structure. Additionally, this methodology should be where onboarding, ongoing reinforcement training, and content should map to. Adding new sales tactics and strategies are most effective for experienced reps who have already mastered their own selling methods. This doesn't mean you shouldn't or can't share some cool articles or resources for these new tactics and strategies - especially cool non-enablement resources and tools they can use to implement those methodology-mapped skills. A good example of this is how to sell through social media, where selling skills like good discovery, creating interest, and driving the next steps, etc. can still be incorporated into this new selling channel. Sharing knowledge should be part of the Sales culture. However, enablement programming should prioritize established methodologies for consistency and to make your impact measurement as easy as possible. 

This is a great question and a task that I was asked to take on for Vanta twice over the past two years - first helping us break into the mid-market, and later helping us break into the enterprise. My first piece of advice is to make sure that there's cross-functional alignment in your company around the desire or need to move upmarket. It's really important that the entire company is on board with this decision. From there, I'd have representatives from GTM and EPD take a long hard look at any "upmarket at bats" that your company has had to date, listening to Gong calls, reviewing Salesforce data, etc to see what's working and what isn't working. You'll want to have the best assessment that you can have on whether or not your product is ready to move up market, where the gaps are (or might be), and whether or not those gaps can be resourced and built. You'll also want to make sure that you have the best initial pulse possible on who your upmarket ICP is. i.e. How are they similar or different to your current ICP? You probably won't know this initially, but you'll figure it out. Finally, you'll want to make sure that you're being thoughtful with how you (in sales) are going to approach generating and working these deals - probably setting aside a small team of sellers to help with the testing. Moving upmarket is generally a tough assignment from my experience and one that really only has a shot of "working" or "feeling good" if your company allocates real cross-functional dollars and resources to it.

Common mistakes include: * Focusing on why you want to work at X company, but not why you want Y job (it's arguably more important to show why you're drawn to the role that you will be doing every day rather than just the company you will be joining) * Not having any questions whatsoever for your interviewer at the end (it's important to show that you took some time to think through thoughtful questions) * Spending more than half the interview going through every single job you've ever had (essentially, reading off the resume). Perfect your elevator pitch for yourself. In just a few minutes, how can you tell your story effectively and succinctly? * Indicating that you've never had any setbacks, failures, or difficulties in your previous roles (no one is perfect so being able to speak to setbacks and what you've learned from them is important) * Not knowing much about the company, its products/services, value props of what you would be selling, etc. (little-to-no research done before the interview shows a lack of Investment on the interviewee's end)

Our top reps excel at spotting potential opportunities. Since we're focused on run-rate tactical deals in the form of additional license, new initiatives, and pilots, our main stakeholders are typically at the VP level or below. The key here is mastering the art of tailoring conversations - distinguishing between "above the line" and "below the line" discussions ensures that our messaging aligns with the audience. In larger enterprises, industry trends and company direction are often widely available. It's crucial to delve into these trends, gaining a deep understanding of industry challenges and directions. This forms the basis for crafting a unique perspective that resonates not only with the business but also its key players. Once everyone's on the same page and the problem is crystal clear, we can then propose a forward-thinking solution that drives them towards their desired outcomes. What sets this approach apart is its emphasis on discovery. Rather than leading with a product pitch, we invest time in understanding the company's priorities. This makes our interactions much more aligned with the client's needs, creating a more genuine and less "sales-y" experience. This method ensures that our solutions aren't just one-size-fits-all, but tailored to fit the precise needs of each client we engage with.

YES! I highly encourage candidates go "above and beyond" in preparing for interviews, because the interview is your opportunity to show the best version of yourself, and I want to build a team of incredible salespeople who are willing to do "above and beyond" for our clients and prospective clients. If you're not willing to go "above and beyond" to get a job, then how I can trust you are going to be willing to go "above and beyond" to close a deal? This can be done before, during, and after an interview: * Before - connecting on LinkedIn or finding their email ahead of time to convey your interest in meeting with the interviewer & aligning on expectations * During - creating a presentation to showcase a deal review or outline your 30-60-90 day plan in if you were to be successful in landing the role * After - by sending a personalized follow up email with any relevant content (leave behinds, blog posts/articles that related to the discussion, etc.) from the conversation and clarifying your interest & next steps Always look for those ways to standout as the best-of-the-best!

How to convert ClassRoom Enablement into 'real world' experiences Effective account discovery can be the subject matter to be trained on. Normally these enablement sessions would use case studies based on potential experiences that could happen during the account discovery steps, giving insight but no "real world" examples. To convert your training you can do this in five simple steps. 1. Use an example case study - this is to expand on techniques for effective discovery. 2. Get each attendee come prepared with three accounts they can work on during the workshop. Create exercises that allow time for them to work on their own account discovery during the workshop. This will allow them to apply what they learned directly to their own accounts. 3. Get feedback from each group. What did they uncover during the exercise? Encourage feedback. 4. During their discussion allow the class to share their own approach to discovery expanding on their experience with the "own account" exercise. 5. Make sure you have a note of all the accounts they have worked on during the sessions to prove the value of these workshops. How to scale this across an organization in 3 simple steps. 1. After running a few sessions you should be able to prove the value of the workshop. Build documentation outlining the number of accounts that were worked on during the session and quantify the pipeline value. 2. Once you have secured agreement from stakeholders to run this workshop at scale get volunteers from the Sales community, you can then train them to assist in the roll out globally. 3. It is critical to schedule sessions in advance as well as having back up trainers ready just in case. Measure the success of the program and keep your stakeholders informed of the success of your program.

Without feedback, you're building & delivering learning in a vacuum and not setting yourself up for success. To mitigate this: * Collect feedback early & often * Send a 5 question (or less) survey after a learning module * Host a debrief where learners can provide topical feedback in-person (or remotely) * Take the feedback & make meaningful changes & tweaks to your training & programs * Repeat each time there is a significant change - better, better, never best