The best sales candidates are able to demonstrate their curiosity, coachability and empathy in the interview process. These are three attributes that we see in our most successful Account Executives and here's why they are important. * Curiosity enables sales reps to uncover valuable insights that can inform their sales approach and tailor solutions to meet the customer's specific needs effectively. Their thirst for continuous learning enables sales reps to stay ahead of the curve, competitors and adapt to changes in the market (especially now). * Coachable sales reps are open to feedback, learn from experiences, and are receptive to new ideas and perspectives. They actively seek out opportunities for growth and ask for feedback to enhance their approach. * Empathetic sales reps build trusting relationships, understand customer needs, communicate effectively, and can more easily resolve objections. Through Gong we are able to track when Account Executives demonstrate empathy and those reps with high levels of empathy are almost always at the top of the leaderboard.

The fundamental sales OKRs are Revenue, Pipeline and Activities leading to pipeline generation. Pipeline generated x Average Sales Price x Close Rate = Revenue Modern sales tools will provide you with plenty of KPIs, however, the context and the priorities of the business will determine the importance of individual KPI. If the business wants to grow by productivity increase rather than headcount growth, the Productivity Per Rep (PPR) is a key driver. Sales Cycle, Close Rate and Average Sales Price become increasingly important. If headcount growth is a key driver then Average Tenure, Attrition, Time to hire/ramp etc. become more relevant

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.

I think there’s a lot to be said about optimizing sales processes with AI. As software continues to improve this will allow AEs to be more productive, manage larger books of business, and deliver highly customized outbound messaging. That said, given the sheer volume of outreach prospects receive today, it’s more important than ever to differentiate yourself, build your network, and establish yourself as a thought leader in your space. If I were an AE starting today, I’d focus on what I want to specialize in and start building relationships—not just with prospects and customers but also with partners in the ecosystem.

As important as any KPI is why the metric is being measured, how you intend to reliably collect and review the data and the frequency you will get together to review the trend good or bad. In entering new markets, however difficult and unpredictable, you need to establish what you do believe to be true: size of the TAM, ICP definition and owners of each stage and target conversion of part of the funnel. Once you commit to the process - and give enough time for the work to show meaningful results, perhaps then can discuss what might feel arbitrary. If after all that there is still uncertainty about what goals might be realistic then commit simply to make improvements each week until there is enough data to set the right goal. Or take a leap of faith, set the goal and over communicate how and why you set it and what you'll do and why if you need to adjust at some point.

You have to have a glutton for punishment moving from structure to no structure, take it from me, but it can be such a rewarding and fulfilling experience to build something from 0→1. Throughout my career, I wouldn’t say there have been many surprises, moreso ‘opportunities’ to put a positive spin on it. Systems & Reporting: We forget how easy we have it being at a larger organization where you have countless resources for technologies that have already been vetted and rolled out, and full funnel reporting to support pipeline/revenue trends, forecasting predictability, etc. * My advice for any revenue leader starting from scratch is to bring in a RevOps hire. This is the most critical investment you can make to build the foundation for your revenue motion. Market Positioning & Value Prop: Don’t expect a clear deck with clear customer case studies, ROI metrics, customer facing collateral, competitive positioning, discovery questions, pitch scripts, etc. As the first sales hire, you must build this. * My advice: Customer tour of duty. This is your opportunity to connect with customers to understand how they use your product, what’s resonating, what needs improvement, etc. Pipeline: You likely won’t have a marketing engine generating inbound leads, let alone an outbound engine targeting key accounts that have high propensity to engage with you. * My advice: Partner with RevOps to understand your target audience by: * Defining your ICP: company size, industry, revenue, geographic location, and technology stack * Leveraging Data: CRM, historical deals, and win/loss analysis, inbound analysis, etc. to find patterns in successful accounts * Intent & Firmographic Data: Third-party tools to gather intent signals (hiring, tech stack, funding, ICP profiles, etc.) and firmographic information (company size, geo, industry, etc.) Hiring: Do not rush this. As the first sales hire, you should be running every single deal for the first 30-60 days. Deeply understand your customers, their challenges, and how you can solve them. * My advice: You must fire “Full Stack AEs” who have something to prove and are willing to hunt, convert, close, and expand. Bring on talent who can do it all. Less is more and remember to hire for the innate skillsets that you cannot teach: grit, humility, curiosity, high EQ, perseverance, hunger, etc. Product & GTM Alignment: This is one of the most critical relationships to get right if you want to grow your revenue engine. * My advice: Create a shared vision with Product and how you plan to differentiate in the market. Create a consistent and clear feedback loop between you and your revenue team and Product where you sync often to understand which key features, workflows, and customer requests would impact the most ARR if rolled out. Communication is key, but ensuring you cut out the noise from one off feature requests is most important. Decisions should be made in a binary and objective approach (ARR).

Transitioning to sales from a different field is very achievable, especially if you can leverage transferable skills and adopt the right strategies. Here’s a step-by-step guide on how someone from another field can successfully make the transition: 1. Identify Transferable Skills • Communication: If your previous role involved a lot of client interaction, negotiation, or presentations, those skills directly apply to sales. • Problem-Solving: Sales is about understanding customer needs and offering solutions, so any experience where you solved complex problems will be useful. • Relationship-Building: If you’ve worked in teams, led projects, or engaged in stakeholder management, these are key to building trust and rapport in sales. • Project Management: Managing a sales pipeline is akin to managing a project. If you’re used to juggling tasks and deadlines, this can translate well into handling leads and closing deals. 2. Learn the Fundamentals of Sales • Study Sales Techniques: Familiarize yourself with basic sales concepts such as lead generation, prospecting, qualifying leads, and closing deals. Books like “SPIN Selling” by Neil Rackham or “The Challenger Sale” by Matthew Dixon can give you a strong foundation. • Understand the Sales Cycle: Research how the typical sales cycle works—from initial contact to closing the deal. Understanding the buyer’s journey will help you hit the ground running. • Master Sales Tools: Get comfortable with sales tools like CRMs (e.g., Freshworks CRM, Salesforce). Many CRMs offer free trials or tutorials to help you understand how to track leads, monitor sales pipelines, and generate reports. 3. Leverage Your Industry Knowledge • If you’re transitioning into sales within your current industry, you already have a huge advantage—product knowledge and industry insights. Use that to position yourself as a consultative salesperson who understands the customer’s challenges from the inside out. • Example: If you’re transitioning from IT to tech sales, your deep understanding of technology will give you credibility when discussing solutions with prospects. 4. Build a Network & Seek Mentorship • Connect with Sales Professionals: Reach out to salespeople in your network for advice. Attend sales-related webinars or join LinkedIn groups focused on sales. • Find a Mentor: Seek out a mentor who has experience in sales. They can offer valuable insights into how to approach sales, navigate challenges, and accelerate your learning curve. 5. Take Sales Training Courses • Online platforms like Coursera, LinkedIn Learning, or Udemy offer sales training programs. Taking courses on topics like prospecting, negotiation, and closing techniques can help build your confidence. • Some programs even offer certifications, which can boost your resume and show potential employers that you’re serious about your transition. 6. Start in a Sales-Adjacent Role • If you’re hesitant to jump directly into sales, consider a sales-adjacent role like customer success, account management, or business development. These roles give you exposure to customers and help you develop sales skills without the direct pressure of meeting quotas. • As you grow more comfortable with client interactions and identifying upsell opportunities, transitioning into a full sales role becomes easier. 7. Highlight Relevant Experience on Your Resume • Tailor your resume to showcase how your previous experiences are relevant to sales. For example: • If you managed relationships or handled negotiations in your previous role, highlight that as evidence of your ability to close deals. • If you analyzed data or market trends, emphasize how that translates into identifying potential customers and understanding the competitive landscape. 8. Prepare for Sales Interviews • In interviews, be ready to discuss your transferable skills and demonstrate how they apply to sales. Emphasize your ability to learn quickly and your passion for solving customer problems. • Example: If you’ve worked in a fast-paced environment before, you can explain how that prepares you for managing multiple leads and deadlines in sales. 9. Learn to Handle Rejection • Sales involves a lot of rejection, so developing resilience is key. Start practicing handling rejection early on, whether it’s in networking or smaller tasks like cold emailing. 10. Start Prospecting • While you’re learning the ropes, start practicing prospecting—research potential customers or industries where you see value, and begin reaching out to them. Even if you’re not in a sales role yet, this will help build confidence and prepare you for future sales interactions. Key Skills to Highlight for the Transition: • Communication & Negotiation • Customer Understanding & Empathy • Project or Relationship Management • Problem-Solving • Team Collaboration & Leadership Conclusion: • Transferable skills from other fields, such as communication, problem-solving, and project management, will help you succeed in sales. • Build a sales knowledge base through study, mentorship, and sales training to understand the core fundamentals. • Leverage your industry knowledge (if applicable) to bring immediate value as a consultative salesperson. • Network and seek mentorship to gain insights from experienced sales professionals and ease your transition. By focusing on these areas, you’ll position yourself as a strong candidate in your new sales career.

KPIs are helpful in unpredictable markets, because they remove a layer of uncertainty. If everyone is making 100 calls per day, and then pipeline generation expands across that channel, then we can help validate that channel - we can then properly inspect other indicators for success in this: what time of day are people calling? What are they saying on the phone? What is their call to action? Frequently, sales teams are lead by the unpredictability of a market and get swept away by a specific pitch, a singular customer response, or a particularly lucky day that a rep was having. Successful KPIs will provide a range of outcomes for each action (good/bad/indifferent), but will still allow for predictability at the top of the funnel (demand planning / capacity planning), the middle of the funnel (demos, meetings, on sites, etc) and bottom of funnel (quotes distributed, scoping calls held, ROI exercises held). Very thoughtful question — hope this helps + very interested to hear other voices on this topic!

KPIs drive the behavior you expect to see from your Sales team. Quota attainment is typically the primary focus for Sales teams, how you achieve those results can alter the direction of your business. Quota from New Logos vs Expansion customers, will impact your future revenue streams differently. Selling a core product vs cross-selling additional products can drive customer retention and ultimately impact churn down the road. Landing a monthly contract vs multi-year commitment allows you to invest more confidently for the future. Identify what's most important for your business and hold your sellers accountable to them. Revenue alone should not be the only KPI for your Sellers.

When you have a small sales team responsible for multiple products with complex features, dividing the workload effectively is critical for both short-term success and long-term growth. Here's how I recommend approaching this challenge: Leverage Cross-Functional Collaboration: * Partner with Internal Experts: Given the complexity of your products, it's essential to collaborate closely with your cross-functional partners, including co-founders, technical staff, engineers, and product managers. These individuals bring deep product knowledge and can provide invaluable insights during sales cycles. * Curate an Ideal Sales Cycle: Work with these internal experts to curate an ideal sales cycle for each product. This involves mapping out the buyer’s journey, identifying key value propositions, and understanding how different product features align with customer pain points and objectives. Document these insights so that they can be easily referenced during sales calls. Pre-Call Preparation: * Comprehensive Briefing: Before every sales call, ensure that your team is thoroughly briefed. This preparation should go beyond simply outlining the agenda. You need to guide your team on how to perform on the call—what communication style to use, how to address the prospect’s business objectives, and which value propositions to emphasize. * Define Call Objectives: At the beginning of each call, clearly establish the intended outcome. One effective technique is to start by saying, “My objective for today’s call is...” or “If I’m successful, by the end of this call you’ll be thinking, feeling, and saying the following...” This sets a clear expectation for both your team and the prospect, ensuring everyone is aligned on the goals of the conversation. Divide and Conquer: * Specialization by Product or Feature: In the short term, consider dividing responsibilities among your team members based on product lines or specific features. This allows each salesperson to become an expert in a particular area, making it easier to manage the complexity of your offerings. * Rotational Coverage: Alternatively, implement a rotational system where each team member takes turns focusing on different products or features. This can help distribute the workload more evenly and build a broader knowledge base within the team, which is beneficial as the team grows. Create a Knowledge Repository: * Centralized Documentation: Develop a centralized repository where all curated sales cycles, value propositions, and product details are stored. This resource should be easily accessible to both your sales team and cross-functional partners, ensuring that everyone is equipped with the information they need for successful calls. * Ongoing Updates: Regularly update this repository as new insights are gained or as products evolve. This dynamic resource will support your team’s ability to adapt and respond to changing customer needs. Feedback and Continuous Improvement: * Post-Call Debriefs: After each call, conduct a brief debrief with your team and any cross-functional participants. Discuss what went well, what could be improved, and how the call’s outcome aligned with the initial objectives. This feedback loop is crucial for refining your approach and improving performance over time. * Iterate on the Process: Use the insights from these debriefs to continually refine your sales process and the way responsibilities are divided. As your team grows, this iterative approach will help you scale more effectively while maintaining the quality of your sales efforts. Focus on Long-Term Growth: * Develop Future Leaders: As your team expands, start identifying potential leaders who can take on more responsibility and eventually lead specialized teams. Invest in their development by giving them opportunities to manage complex sales cycles and work closely with cross-functional partners. * Scalable Processes: Ensure that the processes you establish are scalable. What works for a team of two may not be sustainable for a larger team, so continuously assess and adjust your approach as the team grows.