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.

From a mental perspective burnout is definitely a real challenge in sales. I answered another question in how to handle burnout, as a career in sales is a marathon not a sprint. From a tactical perspective, one of the biggest frustrations I have experienced as an AE are constant book-of-business (BoB) or territory changes. AE's can really hit their stride when they can consistently work their BoB, and sudden, unexpected changes can be disruptive to productivity and revenue. Building a strong BoB is one of the hardest part of sales, once the foundation is set I like to give things time, watch reps cook and allows the “magic” to happen. *This is of course if the current BoB/Territory alignment is working.

So much of the sales KPI tracking has been automated (# meetings, Pipeline generated, funnel progression) so I find the manual ones more difficult to track, but move the needle the most. ie: how many on-sites did a rep conduct this quarter? It's a manual process for reps to log into a CRM and update a meeting field as "in person" and often gets over looked in an organization. There is no substitute for in person meetings. Another example that's difficult to track things like how many new business units or contacts from other business units you broke into in a month, quarter, or year.

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).

* A clear perspective backed by data and customer examples * Brevity while still ensuring substance * Creativity in finding solutions that may not align perfectly to only the thing you had in mind. I screwed up both these things on two separate occasions in highly visible roles where the cost to me (and my sanity on the days that followed) wasn't small. I didn't let the work nor my commitment to finding a suitable resolution fade into the background. Instead I doubled down my commitment to find creative solutions, digging more deeply into the data and customers and using 1:1s and quick actions to show my commitment to seeing solutions through.

Great question! A big one too…for a startup GTM hire looking to develop and own KPIs, I’d recommend working with leadership to align to the KPIs that are most imperative to driving success for your business. For a startup, it can look like steps to traction in a space, or finding the first few customers — in that case, focus your KPIs on pipeline generation, lead creation, and more. I’d even say that you should be setting KPIs for inverse ICP discovery—what are we learning about the market that we should not be in? For a more established company, focus on owning KPIs that are within your realm of action. If you can’t influence the KPI, you’ll be hard pressed to meet them.

Effectively breaking down the quarterly/annual sales goals across all levels within the sales org is the most effective way to get buy in. Be transparent about the role each person will play in helping the team reach the overall goal and emphasize the significance of their contribution and how it impacts the bigger picture.

KPIs are best socialized in the largest setting, where they are relevant for all stakeholders. This establishes transparency and consistency for those who it applies to. For smaller companies this might be a Sales All Hands, while larger organizations might be done in a Team Meeting. Of course, you'll want to allow for questions and clarity to be proven. This can be done in either a group setting, but I also suggest you give space in a 1:1 for nuanced questions to be addressed. Every seller should be crystal clear on what their goals are and how they are being measured. Once your measurement period is up, whether that be monthly, quarterly, semi-annually, or annually, it is important to reflect with your seller on their specific performance and how it compared to expectations. Speak about what they did to exceed expectations (have them share best practices with their colleagues) as well as what got in their ways from achieving expectations (coaching opportunity on removing obstacles). KPIs should not be a secret and how sellers are performing against them should be very transparent. Do your sellers a favor and don't sugar coat the performance. Clear is Kind.

Like anything, as a company grows, priorities change. It's hard to say how Key Stakeholders from other departments change (in this example) but in every growing business I've ever been a part of, what really matters is alignment to the mission. If Stakeholders' roles are impacted because the mission is evolving, this is where you'll see big moves or changes across the stakeholder landscape. Stay close to the stakeholders who have a clear understanding of the mission, and make sure its the same mission your C-Suite is aligning the company against. These are the people you'll want to align yourself with as a company grows/changes as they're the ones who will see you're commitment in the face of uncertainty (change is always uncertain) and they'll likely call you up for a chat to see how you can be used knowing that unwavering commitment to the big picture is valuable.

Receiving critical feedback, especially when you don’t agree with it, can be challenging. However, how you handle it can determine your growth and relationship with your boss. Here’s a step-by-step guide to approach such situations: 1. Stay Calm and Open-Minded • Listen Actively: Even if you don’t agree, listen carefully to the feedback without interrupting. Try to understand the perspective behind the criticism. Often, emotions can cloud how feedback is received, so remaining calm helps you process the information more clearly. • Separate Emotion from Content: Feedback can feel personal, but it’s important to separate your emotions from the critique. Focus on the substance of what’s being said rather than how it makes you feel. 2. Ask Clarifying Questions • If you’re unsure about certain points or don’t fully understand the feedback, ask for clarification. For example: • “Can you give me a specific example of when you observed this behavior?” • “What would success look like in this area for you?” • By seeking clarity, you can ensure you fully understand what your boss is pointing out and how they’d like you to improve. 3. Reflect on the Feedback • Objectively Assess: Before dismissing the feedback, take time to reflect on it objectively. Ask yourself: • Is there any truth to this feedback, even if I don’t fully agree? • Could this be a recurring theme I’ve heard before from others? • Is there an opportunity for growth here, even if the feedback wasn’t delivered in the way I’d prefer? • Talk to a Trusted Peer: Sometimes, seeking an outside perspective from a trusted colleague or mentor can help you see if there’s validity to the feedback. 4. Engage in a Constructive Discussion • Frame Your Response Thoughtfully: If you still don’t agree with the feedback, approach your boss with a respectful and constructive attitude. Acknowledge their perspective while sharing your viewpoint. For example: • “I understand your concern, but I believe in this case, my approach helped achieve X result. Could we discuss what you would have preferred in that situation?” • Be Solution-Oriented: Rather than arguing, focus on finding solutions or alternatives. You can say, “I’d like to understand how we can bridge this gap moving forward. What specific steps do you suggest I take?” 5. Provide Evidence or Context if Needed • If you believe the feedback doesn’t reflect the full picture, provide data, context, or examples that support your perspective. For example: • “I see where you’re coming from, but here’s some additional context you might not be aware of.” • Be factual and avoid sounding defensive. This helps build a constructive dialogue instead of making the conversation adversarial. 6. Create an Action Plan • Agree on Specific Next Steps: Whether or not you agree with the feedback, it’s essential to create an action plan that addresses your boss’s concerns. Ask for specific, measurable outcomes they want to see and agree on a timeline for improvement. • Set Milestones: Break down the feedback into actionable steps and request regular check-ins to ensure you’re on the right track. 7. Know When to Let Go • Not all feedback will be 100% accurate or fair. If, after careful consideration, you still believe the feedback is off base, you may need to respectfully move on without dwelling on it. Focus on the areas you can control and improve, and don’t let one piece of feedback derail your overall progress. 8. Strengthen Your Relationship with Your Boss • Show Initiative: Demonstrate that you’re willing to grow by seeking additional feedback over time, showing proactive efforts to improve, and regularly discussing your progress with your boss. • Build Trust: The more open and professional you are about handling feedback, even when you disagree, the more trust you build with your boss. This can lead to more balanced and constructive feedback in the future. Conclusion: When you receive critical feedback that you don’t agree with, the key is to stay open-minded, seek clarity, and engage in constructive dialogue. Even if you don’t fully agree, reflecting on the feedback and addressing your boss’s concerns professionally will show that you are committed to growth and improvement