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. 

By far the most over-hyped KPI is total pipeline created. This is certainly a key metric to track week over week as a health check, but it provides little insight into what's actually going on. The problem with total pipeline created, is at no point should the conversation end with that KPI. If it's low - why? If it's high - why? Was it one large opp? Was it a bunch of baby opps? Was it quality pipeline? Was it from one AE/Segment/Business Unit - or is everything firing on all cylinders? At best it provides directional guidance to tune into major variances and inspect. At worst it provides false confidence in a pipeline that won't get you to goal. Typically addressing total pipeline creation falls into one of two camps: 1. Mention & move on. These are meetings where the metric is called out, compared to last week and it's either * Good - "great job, let's see if we can stretch this 10% higher next week" * Bad - "we really need to prioritize pipe gen this week. Get on it." 2. Paralysis by analysis. These meetings show the metric, and then dive into 40 slides with individual permutations of how everything performed over the past week; leading to information overload and very little insight into what actually needs to change. This is why instead of just tracking total pipe creation - we want to take a three-pronged approach: 1. How are we tracking towards our pipeline generation goal (which is a leading metric against future bookings)? 2. Identify the factors that are contributing to the current results. 3. Define strategies to optimize the path to goal The standard discussion described above hits the first objective, skips number 2, and the only strategy is often "do more." We could write an entire post on steps 2 and 3, but here are a few variables that can take your basic "total pipeline creation" reporting to the next level * # of opportunities created & average opportunity value. This controls for the one big opp skewing results. You generally want more big deals, but don't want to have to rely on only one big deal to hit the goal. This helps monitor quality & quantity. * Split by region/segment/AE's - this allows you to identify people and parts of the business that are doing well and understand why (do more of it, share learnings, double down). It also ensures that those who aren't doing well don't hide behind overall success of the business and get neglected. We want to identify why they're struggling, and ideally get them unstuck to improve performance. * Pipeline by opportunity source - attribution can lead to some sticky conversations, but tracking where the pipeline is coming from is necessary to improve the overall output. This isn't meant to start a blame game, but you can't optimize something you don't measure. So if AE's, SDR's, Marketing, Partnerships, or PLG is slacking - what can we do about it? If something is working incredibly well - how can we do more? * Pipeline conversion metrics - how is the pipeline that's coming in converting through the funnel to closure? Are disco to demo conversion rates improving, declining or staying the same? What about win rate? Any new trends where we should ride the wave? Anything that's not working which we should stop doing? These metrics will give you a much deeper understanding of the factors that contribute to current results and lay a strong foundation so you can define strategies to help optimize results. With a strong team and partners in marketing, partnerships, SDR and RevOps leadership - you're a brainstorming session away from having your best pipeline generation quarter yet.

As a Sales professional we are often under a lot of pressure to close deals and meet our targets. If you're not careful you can quickly burnout especially when quotas reset each month or quarter. Over the years I’ve had to become more intentional in creating boundaries and finding new ways to recharge. Here are some ways that I’ve found success to prevent burnout and recharge: 1. Prioritize self-care: Prioritize self-care activities such as exercise, meditation, and getting enough sleep. Pay yourself first physically and mentally to stay energized and focused. 2. Take breaks: Take regular breaks throughout the day to rest and recharge. This could include going for a walk, having lunch with a friend, or breathwork between meetings. I also plan a trip each quarter to make sure I'm spending quality time with the family. 3. Set Boundaries: Improving my time management skills and creating clear boundaries between working hours and personal/family time. This can help you prioritize tasks and manage your workload more effectively.

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.

OKRs can vary depending on how your specific business and team are measured. It is crucial to first understand what the business OKRs are before you can be prescriptive in delineating key objectives to your respective team. Team metrics: * Data trends - SCL, ACV, WR + pipeline (3x) * Days within stage * ACV (average contract value) * ASC (average sales cycle) * Delineated by stage * WR (win rate) * Delineated by stage * New logos * New logo vs. expansion revenue * SQO to SAO production (sales qualified to sales accepted opportunity) * Your team should have ~3-4x pipeline coverage in order to feel confident in attaining the number * Activity to SQO production (how many activities until a meeting is booked) * % to quota attainment * There is a fine balance. ~125%+ attainment across the team to me means the number is too attainable. I like to see performance average ~90-95% attainment across a team by region. Business Metrics Great metrics to ask in an interview * Run rate vs. growth rate * Path to profitability * At scale, do these unit economics work? * Revenue now vs. targets for the year vs. projections * Revenue streams * Market share * CAC (Customer acquisition costs) * NDR (Net dollar retention) * What is the current valuation vs. projection for next year

Coming into an organization as the first sales hire puts a lot of responsibility on your shoulders. You are basically in charge of proving the validity of this function within the company. There are a few things that I would consider and act on in this position: Start with the short term. As a first hire in a sales organization, you are required to deliver results that have a very immediate impact that meets the business needs. This means focusing on some low-hanging fruits in order to deliver results within a short time frame. Build a framework. As a first hire within the team, you should make sure you document your work, and create clear guidelines and processes, with the expectation of adding additional members to the team in the future. This will ensure a smooth expansion of the team while positioning you as a thought leader and a pivotal member of this function. Go beyond your scope. As a junior sales hire, never underestimate the power of tenacity. I always invite my team members to push the boundaries and look for additional scope and responsibilities whenever they feel capable. This is a very strong signal that you are willing to take on more, and when management will face a new task at hand, they will know they can count on you.

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.

SDR leaders have a plethora of data to work with, but sometimes it is hard to know where to look. A good starting point is to map out your funnel and ensure you have a metric that measures both quantity and quality to determine which steps of the action are below expectations. Take cold calling as an example. In general, the key metric to evaluate the success of your cold calls is the number of cold calls required to book a demo or the percent of calls that result in a demo. Say you are seeing that it takes you 100 calls to book a demo, but you know your industry average is half that. You might be tempted to jump in and do some mock call scenarios, but what if the problem is not your team’s live cold call execution? Your training may not improve your team’s success rate. You must first map out the steps of successfully sourcing a demo from a cold call. 1. Place the call 2. Have the prospect answer 3. Have the prospect agree to a demo 4. Have the demo occur Each of these steps will have its own benchmark that you can compare your rate to. Say you see that you have a very low answer rate, but convert one in three answered calls to a demo. In this case, mock call training won’t effectively raise your demo booked rate. Instead, you may want to train your team on how to mark good numbers and avoid multiple calls to known bad numbers, how to call at effective times, or even look at better lead data options. When looking at any metric, make sure you are gauging both quantity (are you making enough cold calls) and quality (are those calls being answered and are those conversations turning into live deals).

This is a good, and interesting question. Like many of the other questions, answering this properly requires more context, so I'd ask that you DM me to find some time to chat. A couple of questions that come to mind when reading this question include: How similar or different are the ICPs for these two products? What are the ACVs of the products? How do their sales cycles compare? Are your product and marketing teams investing in both of them equally? Etc. While many might know Vanta as automating SOC 2, we have many products that our sales team sells today, and all of those products are pretty complex (the world of compliance is about as subjective as it gets). One thing that we've seen in asking reps to sell multiple products is that they're going to focus on the products that are easiest to sell, and the products that will make them the most money. The art and the science here is being really thoughtful around pricing and packaging methodology, and also sales compensation incentives, so as to drive the results that you're looking for. Once again, hard to answer this one directly without more context, so please reach out to me directly!

Here is my approach to aligning quarterly/annual sales OKRs with broader business objections: * Define business objections: Identify the key regional business objectives for the quarter or year. They should be specific, measurable, achievable, and time-bound. For example, increasing central enterprise region revenue by 20% in the next 180 days. * Determine sales objectives: Based on business objectives, establish sales-specific objectives that support broader goals and are tied to revenue targets. For example, increasing Stage 1 conversions by 20% within the next 90 days. * Assign projects: Assign specific projects to members of the sales team based on their skills, expertise, and areas of responsibility. * Align individual OKRs: Connect individual projects to sales team OKRs by setting individual key results that contribute to overall sales objectives. * Success Criteria: Clearly define the success criteria for each individual project and how they contribute to the overall sales objectives.