Being in sales, we experience challenges on a daily basis. One of the bigger frustrations is having a great quarter or year and then seeing the dial goes back to zero, knowing you need to start all over again. It’s what we all sign up for, but that doesn’t make it any easier of a pill to swallow. As a sales leader, one of the biggest challenges can be motivating reps to maintain consistency. Keeping reps motivated to successfully climb the mountain each quarter is not a one size fits all approach. For some reps, it’s providing growth and development opportunities that keep them driving, for others it’s SPIFs and recognition that helps them get where they need to be. Finding a way to effectively manage your time can be another big frustration. At times, the sheer number of responsibilities on our plate can feel overwhelming. It’s hard when everyone seems to need something from you and there aren't enough hours in the day. I’ve found that it’s important to be as highly organized as possible, prioritize tasks, learn your productivity patterns, block out calendars to complete important activities and schedule breaks to refresh.

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. 

Essentially, scaling a successful sales team all comes down to the people you hire. The members you are adding as part of your team will define the team culture. I always aim to hire people that help create a culture that fosters innovative thinking to enable growth and progress. Similar to adding ingredients to a recipe, scaling should be done slowly and steadily. Try to find the right people who share the passion, vision and values that you foster within the team. At a later stage, after you have found and hired the right people for your team, make sure you are creating a structure that will enable all team members to grow. Eventually, you will scale up to a point where you will need to develop managers within your team. Make sure that you are nurturing the right people that have the qualities that you look for to make them leaders.

In my experience, communicating the performance & progress of your sales team to the company helps to connect all employees to the mission. It can create transparency into the health of the business, aligns individuals within the company more closely to the voice of the customer, and enables you to more easily activate resources when support is needed. On a Daily Basis... * Every time a deal is Closed/Won, a "Congratulations" email is sent out to the whole company, and a Slack message is posted in our "team" channel sharing the details of the deal & the "Win Notes" (ex. the customer, the value of the deal, the "why" behind their purchase, any learnings, and shout-outs to teammates who helped to close the deal) * For the biggest deals or most special wins, I'll also create fun memes showcasing the rep & the customer and share that via Slack & email too On a Weekly Basis... * I'll create a Freehand with 4-5 slides sharing our progress (Closed/Won against Target, Pipeline Generation over the last week, etc.), shouting out the biggest & most prominent deals of the week, and sharing the most relevant & interesting customer stories. Then I'll record a 3-4 minute video walking through the content, adding my commentary & perspective, and then I'll share the video & the Freehand in our "team" Slack channel so everyone in the company can watch it & engage with the content * I also look for opportunities and encourage my sales managers & sales reps to post in our "sales" Slack channel any interesting stories or learnings throughout the week. Sharing snippets from chorus calls, best practices for generating conversations or overcoming objections, and capturing the greatest success stories helps to raise the overall knowledge of the organization. On a Monthly Basis... * During our company All-Hands, I'll provide and expanded version of my weekly Freehand & video, and also look to provide the platform for 2-3 of our sales reps partnered with their account or customer success managers across different segments/regions to share their customer stories with the entire company. And keep in mind...it's as important to celebrate the journey just as much as the wins, especially if you're in an earlier stage organization. Communicating the behaviors, the mistakes, the learnings, and the process behind your sales motion is often even more valuable for your entire organization than the wins alone.

As mentioned earlier, KPIs vary depending on the business and teams specifically. Below are a few metrics that I find businesses neglect to prioritize: * Employee satisfaction * Retention * Burnout and mental health are critical topics managers should be maniacally focused on * Manager call reviews (Gong, Chorus) * Managers should be constantly providing constructive feedback and hearing more from the customers' voice in order to improve performance and sales motions * Delineating engagement by location and persona * Far too often I see leaders report total metrics without the proper insights into trends by geo, title, etc. * Discounts * How often are you bringing in revenue at your list price? * Are we losing deals due to costs? Budget? * Why, how, and when are we discounting and how does that impact the business? * Proposals sent * I’ve seen frontline managers assume that their reps have sent a quote or order when a buyer has reached a certain stage. Never assume. * SLA * How long does it take for your inbound team to follow up with a lead? * What percentage of leads are followed up with? * How quickly do your AEs follow up via email with a summary from a discovery call? * Meeting acceptance rate * % no shows * % conversion by title and location * Conversion rate * Lagging and leading indicators/trends * Opportunity lifecycle * % of opps by stage * Length of stage progression * NPS * Promoters vs. passives vs. detractors * Customer lifetime value

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.

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.

My mantra on career advanement has been always around doing the role before you get the title. I have always asked my manager that apart from delivering on my targets what more can I do for him/her. Specifically around a sales manager moving to a sales director, the biggest difference is from moving to managing ICs to managing managers. It is a very different trait when you are leading 2 or more layers of sales people under you. The shift focuses a lot more from showing the reps how to run the deals to coaching your managers on how to run the business. It is a transition from being too much in the business to moving to being on the business. My biggest learning there is to build more on your Emotional Quotient and leadership skills as you strive for Director+ roles. Having said that, never move away from the customers. Always try to stay connected to the customers to understand the pulse of the market even if you are at a VP or above level. This way you will always stay relevant to the business and also able to make better GTM decisions

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!

There are many KPI's and metrics you can evaluate for pay raises. Ultimately this is situational based on your companies revenue targets, values and policies. I believe there are 3 key factors in justifying a pay raise: 1) Craft: Mastery of your craft and demonstrated ability of your roles key competencies. 2) Impact: Have you had an outsized impact on Revenue and your GTM organizations key objectives. Some of the key KPI's that I look at are Revenue Growth, Attainment, New customer acquisition and Deal size. Secondly is any contributions you have made off the dashboard to impact the broader team i.e. Process improvements, enablement and creating assets that can be used by the team. 3) Behavior: Demonstrating the right behaviours in how you conduct yourself. I.E. Grit, resilience, positivity etc.