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.

Red flags I look for are around tenur in a closing role - The biggest thing I am trying to interview for/hire for is an understanding or even basic personal philosophy on how the candidate drices a process. If I see short stints at sales gigs - I don't immediately DQ as this could mean culture just wasn't a fit - however, I am concerned that with short stints comes a loack of a developed process. It takes time to learn what a great process looks like at a company - you need to talk to a ton of customers, deal wit hdifferent procurement teams, understand materila value versus marketing jargon - If I see less than 2 years, I often wonder what I am missing and how the candidate got through screening - BUT, depending on the role or the person - tenure may not be a good judge of ability With a developed personal sales philosophy - a younger seller without a ton of tenure will be in a far better position to help me visualize how they fit into my org. 

The biggest mistakes that we see from candidates are related to not being prepared for the interview. Failing to research the company, role, or industry before an interview can signal a lack of genuine interest and initiative. Thoroughly research the company, its products or services, industry trends, and competitors, and come prepared with thoughtful questions to demonstrate engagement and enthusiasm. We expect candidates to do their homework on the role, the interviewer and the company, just like we expect of our Account Executives prior to a prospect meeting. Asking questions when the answers could have been easily found online and not showcasing knowledge when they should have studied up on the company is a clear sign of not being prepared.

It's a great question. I believe that all reps are continuously motivated by earning potential and career growth opportunities, regardless of the stage of the company. To get more nuanced, you'll see earlier hires more motivated by the combination of equity and cash, and you'll also see earlier hires hoping to leverage their early arrival to accelerate their career growth (vs later hires). As an aside, one of the real joys of leading and scaling sales teams is rewarding those deserving early hires with promotions, additional equity grants, etc. We've had the opportunity to do a lot of this at Vanta. More broadly, my advice is to spend a lot of time thinking about the design of your compensation plans (revisiting them at least annually) and also to map out levels and definitions for career growth sooner vs later. Make sure that you're putting your team in a spot where they believe they can hit their goals, and where they understand intimately what career growth means for them, and how to unlock it. Easier said than done. :)

Be transparent and share the “why”: Each SDR should be able to articulate the purpose of their role, the rationale behind their goals, and the methodology used to calculate key performance indicators (KPIs). While many teams have robust processes to determine these factors, they often fail to provide transparency to their teams. When metrics are perceived as being dictated without explanation or “handed down”, they become less motivating. Encourage individuality- Find areas where SDRs can flex their creativity, contribute to experiments, and express their opinions. When you go overboard with processes on an SDR team, it takes away the joy from the work and lowers the possibility of discovering impactful ideas. Create a team that defaults to collaboration and praises readily- While a slack channel, shout-out specific application, or kudos google form can be well intentioned, they often go underutilized. We know that if our team has downtime, they are probably using it to update Salesforce. Make giving praise part of an essential process that is already done!

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.

It's essential to first understand the expectations of your sales leadership, common denominators between successful reps who achieve those expectations, and availability of data to your enablement program. Here are a couple of questions to ask before you get started in creating a measurement plan: * What types of habits do they need to be able to do their everyday work by Day 30-60-90 days? * What are the expectations of your leads? Compare this to enablement insights on what can reasonably be achieved based on historical benchmarks. * Which reps have the most successful ramp numbers? What's the common denominator between all of them? * How long is your onboarding program, including reinforcement training after boot camp? * Do YOU have the data and reports that can show comparative data between reps? A lot of these questions really focus on setting benchmarks on four factors which I've seen are generally performable by many teams: 1. Confidence levels (Subjective): What are your reps' confidence levels around knowing and selling your products increasing over your ramp period? Is there improvement over time? Are you asking this based on various categories such as product, sales skills, and tool usage? 2. Lead Assessment (Subjective): Have their leads fill out a scorecard with guided skill categories based on your sales methodology following your reporting cadence. Make sure that there is guidance on what each category means to minimize the need for calibration. 3. Tool usage (Subjective and Objective): Do your reps know how to use their tools? Do they know where they can access the supporting documentation and guidance after their onboarding program? Are they accessing these tools and using them in the first place? How do they measure up to usage benchmarks - focus on effectiveness later after ramp as I recommend that these should be measured after reinforcement training past onboarding/ramp. 4. Activity, Deal Velocity and Attainment Benchmarks (Objective): How many calls are they making? How many prospects are they sourcing and reaching out to? How many deals are at various stages by 30-60-90 days - are they building and moving deals through their pipeline? Are they achieving the benchmarks/objectives your team has set for win rate and ramp attainment numbers? Hopefully, these categories help to start somewhere. Curious to hear what other enablement leaders have used as well.

To effectively manage complex deal structures and negotiations, it boils down to a deep understanding of the customer's objectives and their timeline for achieving them, and most importantly which internal resources they will need to progress the opportunity. Once we've identified the "when," the next critical step is crafting a mutual close plan that outlines the roles of both internal and external stakeholders. However, it's imperative not to develop this plan in isolation. Every facet of our business must be in sync and fully committed to executing this mapped-out strategy. Without explicit agreement and a shared commitment to the timeline, progress can feel like an uphill battle. If it becomes apparent that the customer is not fully aligned with our mutual plan, it's a clear sign that there's a misalignment somewhere in the buying cycle. In such cases, I advocate for taking a step back, seeking realignment, and securing a renewed commitment from the business before moving forward. We understand that priorities shift, personnel changes occur, and budgets may be reassigned. Thus, it's essential to maintain a rigorous qualification process at every stage, ensuring a clear outcome and timeline. While this approach may seem deliberate, it ultimately accelerates the process in the latter stages of the sales cycle. By diligently bringing in the right people at the right time, we maximize our chances of success and create a smoother path to closing the deal.

When joining a startup as the Head of Sales where there hasn't been a dedicated sales team before, it's crucial to establish a solid foundation while driving rapid growth. Here's a breakdown of goals for the first 30/60/90 days: First 30 Days: 1. Understand the Business: * Gain a deep understanding of the startup's product or service, target market, unique value proposition, and competitive landscape. 2. Assess Current Situation: * Evaluate existing sales processes, if any, and identify areas for improvement or gaps in the sales strategy. 3. Define Sales Strategy: * Develop a clear sales strategy aligned with the company's overall goals and objectives. * Determine target customer segments, pricing models, and go-to-market strategies. 4. Build Sales Infrastructure: * Set up essential sales infrastructure, including CRM software, sales enablement tools, and reporting mechanisms. 5. Hire Core Team Members: * Begin recruiting key sales team members, such as sales managers or account executives, to help execute the sales strategy. Next 30 Days (60 Days Total): 6. Refine Sales Processes: * Streamline and optimise sales processes to increase efficiency and effectiveness. * Implement standardised workflows, sales scripts, and objection handling techniques. 7. Train and Onboard Team: * Provide comprehensive training and onboarding for new sales team members to ensure they are equipped with the skills and knowledge they need to succeed. 8. Start Generating Revenue: * Focus on generating initial revenue by closing deals and acquiring new customers. * Identify quick-win opportunities and prioritise efforts to drive early sales wins. 9. Establish Metrics and Reporting: * Define key performance indicators (KPIs) and establish systems for tracking and reporting on sales metrics. * Monitor progress closely and make adjustments as needed to stay on track towards goals. Next 30 Days (90 Days Total): 10. Scale Sales Operations: * Scale up sales operations by expanding the sales team, refining processes, and investing in additional resources as needed. * Explore opportunities for geographic expansion or new market segments to accelerate growth. 11. Customer Feedback and Iteration: * Gather feedback from early customers to understand their needs, pain points, and satisfaction with the product or service. * Use insights to iterate on the sales strategy, messaging, and product offerings to better align with customer needs. 12. Establish Sales Culture: * Foster a culture of accountability, collaboration, and continuous improvement within the sales team. * Lead by example and reinforce core values that drive success in sales and customer relationships. By setting and achieving these goals in the first 30/60/90 days, you can lay a strong foundation for the sales function, drive rapid growth, and position the startup for long-term success in the market.

I avoid burnout in 3 ways: 1. Make your job easier by always having pipeline ready to go. Burnout is most common when a rep feels they need to start over, and then think that maybe they should just start over somewhere else. Always have good prospects to call, pipeline to win, or customers to contact and sell to. 2. Try new sales tactics, but don't stray too far from what has made you successful. Testing and trying new things is fun and spices things up, but do not overhaul your entire approach. Ask that one question you never do and see what happens. 3. Take time off. Salespeople can have major FOMO. I'm going to miss an inbound opportunity if I take off, I know it! If you follow #1 above, vacations, even small ones, will be your best friend. My first 10 years of working, 3 and 4 day weekends were my best ways to recharge!