There's a few different ways to gauge a candidate's autonomy in a sales interview. 1. Behavioral Questions: Ask situational questions that require candidates to describe times where they had to work independently to achieve sales targets or overcome challenges. For example one of my go to questions is, "What's the most creative, out of the ordinary, or above and beyond thing you’ve done to win a customer?" 2. Past Experience: Review the candidate's resume and ask about specific examples where they demonstrated autonomy in previous sales roles. Inquire about their sales process, strategies they implemented independently, and decisions they made autonomously. 3. Problem-solving Scenarios: Present examples of current sales scenarios and ask how the candidate would approach them. Evaluate whether they demonstrate the ability to think critically and make decisions independently in real life situations that arise. 4. Role-play Exercises: Conduct role-playing exercises where the candidate must handle a sales scenario independently. We ask candidates to run a discovery call and give them basic information on the team. Observe how they handle the situation and objections without much assistance or input.

Burnout is a huge challenge for many sales professionals. Many folks in sales burn the candle at both ends - stacking meetings back to back with no break, working 12 hour+ days, and never truly taking a break or signing off. Over time this adds up, and you can get into a pretty demotivated state of burnout as a result. Healthy habits are the solution. There's a company called PeopleFuel that runs a seminar called The Energy Project, that I found incredibly helpful. The thesis is this - you only have so much energy - and things that happen in your day will take away from that energy. Once you hit your 30s, typically demands on your time increase and the energy you have decreases slowly over time. The people that are most resilient to burnout are those that have very healthy habits. The Energy Project breaks this down into Physical, Emotional, Mental, and Spiritual. Physical - do you eat healthy? Do you get regular sleep? Do you exercise regularly. Emotional - Are you self aware to how you feel? Practicing mindfulness / breathwork / meditation all are really powerful for this Mental - The average human probably has 90 minutes of focus in one go. Micro-breaks are essential to "reset" that focus. Can you build in a walk, a quick breather outside, or 10 deep breaths to refocus. Take vacations and fully disconnect. Spiritual - do you have a deep connection to purpose? This could be religion for some folks, charity, or just understanding the purpose in their work and how it fulfills them. TLDR: Even with a monthly quota (and i've had over 160 months of them) sales is a marathon not a sprint. If you take care of yourself with healthy habits, you are wildly more resilient to the stresses of sales quota.

In the first 90 days as a sales leader, focusing on "quick wins" can help demonstrate early success and build momentum for long-term growth. Here are some examples of quick wins you should aim for: 1. Process Optimisation: * Identify inefficiencies in the sales process and implement quick fixes to streamline workflows. * Automate manual tasks or paperwork to free up time for sales reps to focus on selling activities. 2. Low-Hanging Fruit: * Identify and prioritise leads or opportunities that are close to conversion and focus efforts on closing these deals quickly. * Reach out to dormant or inactive accounts to re-engage them and generate immediate revenue. 3. Sales Training and Coaching: * Provide targeted training or coaching sessions to address common sales challenges or objections. * Share best practices and success stories to inspire and motivate the sales team. 4. Pipeline Management: * Review the sales pipeline and prioritise high-probability opportunities that are likely to close within the next 30-60 days. * Provide guidance and support to sales reps to help them move deals through the pipeline more efficiently. 5. Cross-Selling and Upselling: * Identify opportunities to cross-sell or upsell additional products or services to existing customers. * Develop targeted campaigns or promotions to encourage repeat business and increase average deal size. 6. Customer Feedback and Satisfaction: * Reach out to recent customers to gather feedback on their experience and satisfaction with the product or service. * Address any concerns or issues raised by customers quickly to improve retention and loyalty. 7. Sales Collateral and Resources: * Develop or update sales collateral, presentations, and resources to support sales efforts. * Provide reps with tools and materials they can use to effectively communicate the value proposition and overcome objections. 8. Team Alignment and Collaboration: * Foster a culture of collaboration and teamwork by organizing cross-functional meetings or brainstorming sessions. * Identify opportunities for synergy between sales and other departments, such as marketing or customer success, to improve overall performance. 9. Performance Tracking and Accountability: * Implement systems or processes to track sales performance and hold reps accountable for meeting targets. * Celebrate early successes and recognise top performers to boost morale and motivation within the team. By focusing on these quick wins in the first 90 days, you can demonstrate your effectiveness as a sales leader, build confidence within the team, and lay the groundwork for sustained success in the future.

Sales and Customer Success shouldn't be two separate islands. These groups have to be incredibly synced in order to best serve your customer base. This is why I recommend a business hire a revenue leader who oversees both customer acquisition and customer retention. That way, you have an executive who isn't selfishly focused on one area of the business. Roles & Responsibilities + Compensation Incentivization: * Be sure to clearly define roles and swimlanes between AEs & CSMs * Recommend AEs build pipeline, close deals, expand accounts (full stack AEs) * Clearly defined handoff/partnership process once initial land is closed. * Account plans are a must based on mutually identified threshold (i.e. ARR, propensity to scale) * Customer journey mapping: Outline clear partnership touch points from pre to post sales to determine contribution amongst account teams. How might you quantify services for large scale deployments? Don't give anything away for free, use your concession playbook if post sales services are included. * Recommend CSMs renew customers * CSMs incentivized to generate expansion opportunities and will get % payout of net revenue retention (expansion) * Recommend RevOps is also incentivized to hit a revenue target. RevOps is the most crucial partner to your revenue leader. They need incentivization to support the sellers get their job done. Make them feel a part of the team and reward them for their work. * Shared KPIs: * Customer obsessed culture: 1 team, 1 dream, always asking “what’s in it for the customer?” * Pipeline (conversion vs. vanity stats), new business vs. expansion revenue, NPS, retention, churn vs. contraction, product/feature adoption * AEs & CSMs must have have consistent meetings to knowledge share, discuss and implement process improvement, strategize on key accounts, share feedback from the customers, etc. Pairing AEs and CSMs by segment can drive a much more seamless working relationship internally and for the customer Don't forget, hiring A+ talent is what keeps these teams motivated most. People want to be surrounded by high performers. The moment you hire a B player, the entire attitude, work ethic, morale, and throughput of your team completely changes. Never settle for anything less than A+ talent/ * Identify needed skills by role in changing landscape. Don't hire the same profile every time. Find teammates who balance each other out. Look for innate skillsets you cannot coach (persistence, hustle, humility, selfless, grit, competitiveness, hunger) * Performance management: Atomic unit of efficiency * Continuous coaching: Call reviews * Career development: Career laddering across the entire organization. Invest in your SDRs and build a low lift, high return SMB segment to promote them into. * Sell 90 Initiative: * Frontline reps spend 90% of time on customers * Automate/remove as much manual friction as possible from outbounding to accounts to renewing customers. Your customer facing team should never worry about anything other than their customer

There is a give and take with standardizing KPIs but also having enough variance to account for things segment, (Strat, Ent, MM, Growth) number of accounts, and so on. The easiest way to have consistency and also provide a lens to inspect forecast is by implementing standardization when possible. No matter what segment you're in or how many accounts you have, if a deal is 345 days old... that's going to tell me something about the forecast accuracy of the stage it's in. I am a big fan of ensuring reps are training that in the mid point of the quarter or month, whatever your quota and cadence is, deals with a close date in quarter or in month must be in Best Case, Commit, or Closed. Nothing can be in "Pipeline" or "Omitted"

Be clear on your goals and show progress against those week over week. Use that to show the quality of work being done and then be specific on where you're running up against challenges in achieving that plan where more resources can help. Important to show you've thought threw alternative options particularly where there are resource constraints.

Very interesting question — and one that brings up a few more! * Quota attainment is a KPI that is directly meaningful to a seller—if she can hit her KPI of quota attainment year after year, that will be meaningful to her personally! * However, quota attainment isn’t a helpful KPI to the company by itself — we could find out that the above seller is selling bad deals — selling deals that have low margins, high churn rates, and more… This is why it’s important to have a several KPIs that are developed to the needs of the business—and to the needs of the seller. Otherwise, it’s like judging someone’s safe driving ability solely by whether or not they drive the speed limit. Many people drive the speed limit, but are looking at their phone, or are ignoring their turn signals, etc. It’s one KPI that will help inform whether a driver is safe, but it’s not the only way of determining whether a driver is safe.

A challenging question and probably different across organizations. The one that I always find a challenge is the expected volume of outreach emails sent per week. This number could be huge and look great on a dashboard but if the quality is poor, then what good is the volume and what outcome will this achieve? Here we need to be looking at achieving the right balance of activity and being smarter about how we message clients in order to maintain quality. With all KPIs the data can only tell us so much and there will always be a need to delve deeper to truly understand how effective your sales team is.

Good OKRs define the output you are looking to achieve. Be clear in your outcome and give your sellers the space to define their process. Your managers can lean in on process suggestions, if they need help there. It can be easy to focus on effort metrics like volume of calls or emails, however if the true goal is simply the weekly PipeGen that was achieved or amount of revenue that was booked, use them as your North Star. For roles where they also act as Post-Sales/Success, instead of monitoring meetings, you may want to hold the team accountable to product activation, usage milestones, or active users.

When you’re the first sales leader at a company, establishing the function from scratch can be daunting. Here’s how I approach prioritizing needs and deliverables: Leverage Existing Assets: * Build on Experience: Over the course of my career, I’ve created a "treasure chest" of value assets, including quarterly business reviews, value engineering tools, first call decks, sales process templates, and more. I keep these in an off-brand format so that when I join a new company, I can quickly adapt them to the new environment. * Uniform Sales Process: My sales process is relatively uniform across businesses, with key deliverables and milestones defined for each stage. The only adjustments I make are specific to the new company's terminology, product details, and business context. This allows me to hit the ground running without reinventing the wheel. Simplify and Prioritize Key Deliverables: * Focus on Core Deliverables: I prioritize deliverables with the highest impact on driving sales and aligning the team. This includes: * Sales Process: A clear, concise sales process with well-defined steps and milestones. * Key Assets: Such as a business case or value engineering asset, technical review templates, and value-selling principles. These are critical for ensuring the sales team and cross-functional partners are aligned and equipped to deliver value to prospects. * Prescriptive Content: For each stage of the sales process, I maintain a single, major deliverable that serves as the focal point. This could be an agenda slide, a hero’s journey narrative, or a pain menu. Keeping it simple ensures the team stays focused and the process remains agile. Adapt and Iterate: * Tailoring Content: While the framework remains consistent, I tailor the content to fit the business's specific needs. This could involve tweaking the value propositions, refining the messaging, or adjusting the sales collateral to better resonate with the target market. * Utilize AI Tools: With advancements like ChatGPT, it’s now easier to adapt and synthesize past content quickly. I can input old assets into a large language model and generate updated versions tailored to the new business context, saving time and ensuring consistency. Work Ethic and Commitment: * Going the Extra Mile: Establishing a sales function from scratch requires much effort and overtime, especially in the early stages. It’s about doing whatever it takes to produce the necessary deliverables and set the foundation for a scalable sales operation. * Continuous Improvement: As the business evolves, so does the sales process. I continuously refine and improve the framework based on feedback, results, and new challenges that arise.