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.

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.

LIke most professions, you can not lead a team well if you haven't done the job yourself. Must Haves : * You should have been a quota carrying sales rep for at least 3 to 5 years before you can transition into sales leadership. * Have a good understanding of the product. You don't want to be in a meeting with your sales rep where you are not able to answer the use cases and functionalities of your profuct to the customer without any hesitation * Good understanding of the market you operate in * Ability to motivate the team and shield any unnecessary pressure from top management * Good analytical skiils would always help you to identify trends in the market place as well as your own internal metrics * Listening skills : They are both important as a sales rep as well as a sales leader. * Focus on Culture :Though some people might put this under "Nice to Haves", I strongly feel that being focussed on culture and building a strong team culture helps a sales leader a lot. Nice to Haves * Some experience around areas of business development and customer success is always helpful * Project management skills can come in handy as you go up the hierarchy and need to work across cross-functional teams

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? :)

Be prepared: C-Suite folks are busy people- don't waste their time. Ensure you are prepared for every meeting you have with them. Anticipate the questions you would expect them to ask and have your answers ready to reply with in real time. Be clear and concise: It goes a long way in terms of how you show up to the C-Suite if you can articulate what you need to say in a clear and concise way. If you are taking the time to prepare, this should be easy enough to accomplish. Properly prepare them: If you are running a meeting or call together or simply need your C-Suite's involvement in a deal or project you're working on, it is critical to properly prep them for it. Take the extra time to build out a pre-read that outlines the background of the deal or project, who's involved, the goal of their involvement, what you actually need from them, and in some cases suggested ghost written content (i.e. ghost written email in a deal for exec to exec alignment). Simply put, if you are asking something of them, make it as easy as possible for them to get up to speed and execute on it. Be confident: The C-Suite are people too! Of course, have respect, but also have confidence in you and make sure that shines through. 

This is a great question, and how we have done this at Vanta has evolved over the years. Being thoughtful about how sales communicates updates to the rest of the company (and vice versa) is so critical. Today, we have a number of public slack channels where sales or GTM-related updates are regularly shared. We also host a public GTM All-Hands once a month that the entire company is (optionally) invited to attend. We also have monthly business reviews where GTM and EPD (engineering, product, design) representatives are asked to report on progress on key cross-functional company initiatives. All this to say, there are any number of ways that you can (and should) communicate sales updates to the rest of the company. Sometimes even a weekly email is enough to do the trick. H/t to my CRO for sharing that idea!

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.

Great question! There are three specific ways I do this: 1. There are some annual reports done for Sales Enablement that come from third-party sources like Forrester and Gartner. These may be gated, but sometimes they are sent by tools vendors. 2. Use your tool vendor resources! I always ask my CSMs for all the tools we own if they've created an annual trends report or a "best practice' doc for their specific tools whether it's outbound tools, content engagement, knowledge, etc. They have these for their own product/core marketing behind gated sites but since you're already a customer, they should be accessible to you without the barrier. 3. Forums - one I follow is the Sales Enablement Society forum where professionals ask questions. And, I guess we should give Sharebird a shoutout too!

If an account executive is sharing feedback (positive or negative!), here are a few questions you can ask to decide how to incorporate it. 1. Is the feedback specific? To act on feedback, we have to have enough information to properly diagnose the cause. If an AE shares that an account was unqualified, did they share the name of the account and the particular reasoning? 2. Do we know what led to the feedback? To act on feedback, you have to know what to change. Identify the specific behavior or process that led to the feedback. In this case, perhaps there was a qualification question that wasn’t asked or we had incorrect data in the CRM about the account. Different causes require different solutions and we shouldn’t assume the cause. 3. Is this an individual occurrence or a trend? Ask if they have any additional examples for the feedback or even recent counterexamples. Scoping the occurrence of the feedback will help you figure out if you need to work with single individuals or change an overall process. Don’t treat feedback as global unless you have shown a sufficient sample size. Once you have gotten the above information, you can decide how to implement a change (and if a change is worth implementing). If the feedback seems to be coming from a one-off situation, you may want to approach at the individual level. If the feedback seems to point towards a larger trend, you may want to design an experiment or A/B test to see if the suggested changes work. Lastly, make sure to proactively request feedback from the AE team. Their input is particularly valuable for (1) deciding how to prioritize account books and (2) refining your Ideal Customer Profile and even identify new use cases.