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.

Sales stakeholders can come from any department within an organization and as the company grows, their input is key to sales success. A few examples may be: 1. Product Teams: aligning sales strategies with new offerings and/or customer feedback 2. Marketing: greater integration for cohesive messaging and lead gen 3. Customer success: ensuring client satisfaction and retention 4. External partners: distributors, resellers, support partners can help expand market reach The best method to building and maintaining relationships with your stakeholders is to regularly communicate with them. Show appreciation for their support, inform them of changes, address their concerns and involve them in key decisions that may impact their area of the business. Creating trust and consistent communication will help build, or strengthen, your relationships.

This is such a great question! Having been a sales professional since 2013, I completely understand how burnout can arise, especially with the constant "reset" every quarter. What’s helped me is creating clear personal boundaries with work and sticking to a structured, repeatable process. By focusing on the things I can control and holding myself accountable to weekly, monthly, and quarterly KPIs, I’ve built a more predictable and manageable workflow. I view sales as running my own business—it requires exceptional time management and operational efficiency.

Firstly, it is important to recognize that discovery is not one stage of a sales process nor is it only the questioning that occurs on your first meeting. Discovery is a continuous journey of leading with curiosity, probing deeper, summarizing your understanding, and validating your takeaways through the sales process and with each new individual in the sales process. To ensure your discovery is efficient & effective... * Do Your Research & Prepare: the better you prepare for the conversation and align on the answers you need to best identify if/how your solution may be of value to the prospective customer the more effective you'll be able to use your time * Stay Curious: if you engage in curious, open-ended questions you will be able to uncover more critical information than if you focus on a standard set of pre-defined & closed questions * Probe Deeper: don't take just the surface level answer to questions, keep digging deeper to get to the root of their current state, goals, challenges, pain, etc. * Summarize & Validate Your Understanding: always make sure to summarize what you heard and validate you heard that correctly. Ultimately, the underlying business case is your prospective customer's story in their own words, so while you can craft it through discovery, to align on the true narrative, it needs to be in their words. If through your conversations you cannot get the prospective customer to articulate 1) why they need to do anything, 2) why they need to do it now, and 3) why your product is the best solution, then that may indicate you have sufficient holes in your deal which could require you qualifying out.

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"

* 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.

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.

As a sales leader, certain hard skills are essential to drive success, while others can give you an edge but are not necessarily mandatory. Here’s a breakdown of the must-haves and nice-to-haves: Must-Have Hard Skills: 1. Sales Strategy Development • Ability to design, execute, and adjust sales strategies based on data, market conditions, and business objectives. A sales leader must know how to create effective go-to-market plans and align them with the company’s overall goals. 2. CRM & Sales Tools Mastery • Proficiency in Customer Relationship Management (CRM) tools like Freshworks CRM, Salesforce, or HubSpot is crucial. You should be able to analyze pipelines, track performance metrics, and optimize sales processes using these tools. 3. Data Analysis & Reporting • Sales leaders need strong analytical skills to interpret sales data, identify trends, and make data-driven decisions. This includes creating reports on sales performance, forecasting, and setting quotas based on historical data and market analysis. 4. Forecasting & Budgeting • Accurate forecasting of revenue, setting realistic targets, and managing budgets are critical responsibilities. Sales leaders need to project future sales based on pipeline data and market conditions, while keeping an eye on financial performance. 5. Negotiation & Closing Techniques • Sales leaders must have advanced negotiation skills, understanding how to navigate complex deals, and mentor their teams on closing strategies for high-value deals. 6. Market & Competitive Analysis • Strong knowledge of the market landscape, competitor activities, and industry trends is essential to position the product effectively and stay ahead of the competition. 7. Sales Process Optimization • Understanding and improving the sales process is key. This includes implementing best practices for prospecting, lead nurturing, and deal closing to enhance efficiency across the team. 8. Product & Industry Expertise • A deep understanding of the product or service being sold and the industry in which the company operates is crucial. This allows leaders to better coach their team and ensure they can articulate value to customers effectively. Nice-to-Have Hard Skills: 1. Technical Knowledge (e.g., SaaS or Enterprise Solutions) • Depending on the industry, technical knowledge of the product, such as understanding software or cloud solutions in SaaS sales, can be valuable but not always necessary. Having this knowledge can help bridge gaps between sales and product teams. 2. Digital Marketing & Social Selling • Familiarity with digital marketing tactics (SEO, content marketing, paid advertising) and social selling on platforms like LinkedIn can help sales leaders align closely with marketing efforts and empower reps to generate leads more effectively. 3. Sales Enablement Tools & Automation • Knowing how to implement and utilize sales enablement tools (like content management systems, email automation, and AI-powered sales platforms) can boost team productivity and improve alignment with other departments, such as marketing. 4. Customer Success & Retention Tactics • Understanding customer success strategies can help sales leaders focus on long-term relationships and retention, which is increasingly important in subscription-based business models like SaaS. 5. Cross-Functional Collaboration • While not always a hard skill in the traditional sense, the ability to work closely with product, marketing, and customer success teams is crucial for driving sales alignment and organizational success. A familiarity with tools like Slack or project management software (e.g., Trello, Asana) can support this collaboration. 6. Business Development & Partnership Building • Sales leaders who understand how to create and manage partnerships or business development efforts can bring new revenue streams into the business. This is especially helpful for companies looking to expand into new markets or verticals. 7. Sales Training & Coaching • Being adept at designing and delivering sales training programs is a great skill for sales leaders who want to continuously improve their team’s performance. This includes understanding adult learning principles and creating actionable coaching plans. Conclusion: • Must-Haves: Skills like sales strategy, CRM mastery, data analysis, and process optimization are essential for a sales leader to drive and manage a team effectively. • Nice-to-Haves: Skills like technical expertise, sales enablement tools, and digital marketing can provide an extra edge, especially in tech-driven or fast-evolving markets. Mastering these must-have hard skills while building on the nice-to-have skills will ensure a sales leader’s success in guiding their team and achieving business goals.

There are two primary paths for sales professionals who want to continue to level up in sales. The individual contributor path and the management path. Individual contributors might start as an Sales Development Rep or Business Development Rep. These are entry level sales roles that involve appointment setting for a more senior Account Executive who then takes a meeting and works to close business. At most tech companies, the most junior Account Executives work in the small business division, and more senior reps sell to progressively larger segments. So career progression might look like BDR -> Small Business Account Executive -> Mid Market Account Executive -> Enterprise Account Executive On the other side, if you pursue the management track, you may promote in any segment from account executive to manager. Typically this involves taking on leadership responsibilities (something like a team lead program to get experience) and coaching peers to development the management skillset. This could look like BDR-> Account Executive -> Sales Manager -> Director -> VP of Sales.