I think finding ways to give yourself an edge is always in your best interest. You want to avoid creating too much work for yourself, but there are needle-moving ways to get this edge that don't require a massive lift. If you're in a role play interview, treat it like a real sales process. Send a pre-call email with the agenda and goal of the call outlined and send a follow up email in the format you typically would in an active deal. Prepare thoughtful and custom questions to ask each of your interviewers that show how you think, what you care about, and your business acumen and/or natural curiosity.

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.

This isn’t a one size fits all approach. Every leader should bring a different focus to their 30-60-90 day plan based on their leadership style, the stage in which the company is at, industry/market dynamics, immediate challenges/goals, etc. That said, the high level framework below is something I’ve used at several companies which has proven to be quite successful: Days 1-30: Listen, Learn, Connect * Establish presence and connection with team * Roll out User Manuals: How to guides for working effectively with one another * Product, value prop, and competition proficiency * Cross-departmental tour of duty (ally building) * Benchmark data (lagging/leading indicators) * RevOps partnership/hiring is critical * Understand first before suggesting any changes * Understand the challenges specific to the business and team in exceeding targets * Never assume what worked historically will work now * Deeply understand your customers Days 31-60: Align, Implement, Measure * Align before setting unrealistic expectations * Generate path toward exceeding targets * Provide clear measurables on path to targets (SMART goals) * Drive winning culture * Leveraging benchmark data to drive process improvement * Solve process inefficiencies Days 61-90 * Establish virtuous cycle with team and peers * Generate quick wins * Create constructive feedback loop * Scaling a repeatable outbound playbook * Address team and business challenges with clear solutions * Sell 90 initiative: GTM team should spend 90% of time with customers * Performance management: make smart decisions, clearly communicate

I don’t believe there’s a single "right" career path for a sales professional. Sales is an incredible foundation that can lead to countless opportunities because the skills are universally valuable. Whether you’re pitching investors as a founder or advocating for an internal business initiative, you’re always selling—yourself, your ideas, your vision, or your work. Traditionally, Sales careers may start as an SDR, progress to AE, Mid-Market AE, Enterprise AE, and eventually to Client partner or Senior Relationship Manager. Alternatively, you might take the leadership path, from sales manager and graduate to senior leadership roles. Ultimately, your path should align with your strengths and what gets you excited every morning.

When taking on a Head of Sales role, certain red flags may emerge within the first 90 days that could indicate challenges or issues within the organisation. While every situation is unique, here are some red flags to consider that may warrant reconsideration of your position: 1. Lack of Support from Leadership: * If you encounter resistance or lack of support from executive leadership in implementing sales strategies or initiatives, it may signal broader issues with alignment or commitment to sales objectives. 2. Unclear Expectations or Objectives: * If you find that expectations for the role are unclear or constantly shifting, it may indicate a lack of strategic direction or organizational instability. 3. High Turnover in Sales Team: * If there is a pattern of high turnover within the sales team, it could be indicative of deeper issues such as poor leadership, ineffective sales processes, or cultural issues within the organisation. 4. Inadequate Sales Infrastructure: * If essential sales infrastructure such as CRM systems, sales enablement tools, or support resources are lacking or poorly implemented, it can hinder the effectiveness of the sales team and impede growth. 5. Misalignment of Values or Culture: * If you find that the company's values or culture are not aligned with your own, it may lead to dissatisfaction or difficulty in fulfilling your role effectively. 6. Lack of Transparency or Communication: * If there is a lack of transparency or open communication within the organisation, it can lead to misunderstandings, mistrust, and challenges in executing sales strategies. 7. Poor Financial Health or Market Position: * If the company is experiencing financial difficulties or is struggling to compete in the market, it may impact the viability of your role and the potential for success in driving revenue growth. 8. Ethical Concerns or Red Flags: * If you encounter unethical practices or behavior within the organisation that goes against your values or professional standards, it may be a sign of deeper cultural or organisational issues. 9. Overly Aggressive Sales Targets: * If sales targets are set unrealistically high or in a manner that puts undue pressure on the sales team, it can lead to burnout, turnover, and ultimately, poor performance. 10. Lack of Opportunity for Growth or Development: * If there are limited opportunities for career growth or professional development within the organization, it may impact your long-term satisfaction and fulfilment in the role. If you encounter one or more of these red flags within your first 90 days as Head of Sales, it's essential to carefully evaluate the situation and consider whether it aligns with your career goals and values. In some cases, it may be necessary to have candid discussions with leadership or explore alternative options that better suit your needs and aspirations.

I've been at HubSpot for 14 years. Every year I ask myself the same questions: -Do I enjoy the people I work with? -Am I continuously progressing my career and growing my earnings potential? -Are there new and difficult challenges that stretch me and push me to develop new skills? -Am I fulfilled by the work I do? If all the above are yes, I stay in the role. So far, I've been very fortunate to have a great career at HubSpot. When evaluating new companies, I would recommend a few things for folks to evaluate. First off - life stage and relative risk tolerance can be important to think through. If you are early in your career, have a larger appetite for risk, and are willing to risk a "bad bounce," early stage companies are higher risk / higher reward. If you are later in your career and desire more stability, have family earnings obligations, or just want lower risk in general, later stage companies are the right move. Once you've established stage, I like to think about the intersection of your experience and what you are passionate about. Sit down and write a list of industries / areas that get you excited, then also write where you have experience and knowledge. Often where you overlap is a great place to start. Next, I'd make a target list of companies. Companies that have happy customers (in tech you can see customer reviews at G2crowd, trustradius, or other industry sites,) happy employees (Glassdoor,) and a steady growth rate (look at pace of funding rounds, or read their earnings reports if publicly traded,) are a good bet. I'd suggest solving for growth - mid to high growth companies have many more promotion opportunities and your equity will likely go farther. From there, I'd check linkedin to look for connections in your network that are at one of your target companies. Personally, I'd almost never apply through a job listing, I would always reach out to the connection, ask for 15 minutes to chat about the company, and then ask them to refer you in.

To establish credibility and trust, you need to demonstrate your ability and reliability in your actions - consistently. Communicate openly and honestly and show empathy and consideration for other's perspectives while demonstrating your own knowledge and skills. People will trust you if your actions follow your words and you're honest in your communication.

Consistently reviewing and analyzing KPIs can be crucial in helping your sales team adapt to change. For example, if you are moving in to a new market the KPIs will not look the same as the sales KPIs from an established market. Momentum will develop over time. Adding rigor around the need for ongoing KPI analysis is an effective way to help your reps pivot and adapt on a regular basis and will help your reps become more successful in changing markets. In return this will mean they become more realistic when it comes to forecasting the potential of an opportunity, as they will better understand when an opportunity will close based on the appetite of the market at that time.

Re-evaluating KPIs on a regular basis is a healthy practice for your company. Just because it worked this year, doesn't mean those same motions will work next. For instance, in year's past, you may have been okay working with a Business Head to justify budget. Nowadays, CFO's are scrutinizing expenses more than ever, expecting to see the R in ROI. If you are not involving them early, your success rate is likely suffering. You'll want to evaluate the attributes making up your wins vs the deals you lose, before determining what to use moving forward. It could be access to power, Executive alignment, departments involved, breadth of solution to differentiate from competition, on-sites delivered, problems you're solving, or length of sales cycle. Identify your trends and set those as your targets. Then make sure you have a simply process to track the data and hold your sellers accountable.

I think any KPI that is not integrated into the quota and comp structure for any AE by and large is misguided. If you want AEs to focus on specific behaviors then build it into their comp plan and prioritize quota relief over increased commission payments if you have to choose. There are only two exceptions to this in my mind: any KPIs (pipe coverage, onsite meetings, etc.) where you can establish a direct connection to the health of those metrics and their ability to close more revenue OR behavior changes you might want to see mid year, in which case you can use SPIFFs as a tool to align incentives to the behavior changes you want to see. And for any behaviors where the KPIs or SPIFFs are not baked into their quota, be sure to have dashboards that accurately reflect what is happening and commit to communicating regularly progress each AE is making against them. They will otherwise be lost or forgotten about as quota relief and commission always reigns supreme.