The Ultimate Guide to Hiring a VP of Sales for Your B2B Startup: From Early Stage to Scale (Part-2)

Evolution Equity Partners
6 min readMay 21, 2023

Part one of the story helped you identify your company’s growth stage and the type of VP of sales it requires. But how do you go about finding the right person? What should you ask during the interview process? What to look for in the answers? In this section, we’ll discuss the questions you should ask during the interview process and what to expect in the answers to ensure you make the right choice.

There are at least six topics that you should focus your interview on:

  1. A span of control & management
  2. Sales capacity planning and budgeting
  3. Funnel analysis practices
  4. GTM strategy from the ground up
  5. Deal management
  6. Market/vertical-specific experience

The span of control & management:

In this topic, you should learn about your candidate’s management skills and experience in the last two to three positions. Your questions should cover a broad range of topics related to the management of sale steam. You should expect to hear a few key points when answering your questions. The points are:

  • Team size over the last three years
  • Key functions in the team — SDR, AE, AM, RevOps
  • Team’s location — office, WFH, remote offices
  • Probation, PIP (performance improvement plan), and terminations criteria
  • Type of team meetings/management interactions: 1:1s, group meetings, awards, celebrating wins
  • Evaluate new hire ramp and progress
  • Coaching, pitchback training
  • Sales kickoff & all-hands meetings
  • Objection handling

Example of questions you can ask:

  1. Can you walk me through your experience building and managing a sales team, including your leadership style and how you motivate and develop your team members?
  2. How do you approach collaboration and communication with other departments, such as marketing, product, and customer success?
  3. Can you describe your approach to determining the optimal span of control for sales teams?
  4. How do you ensure that each team member can receive the necessary amount of attention and support from their manager?
  5. What metrics do you use to evaluate the effectiveness of your span of control strategy, and how do you use them to make adjustments as needed?

Sales capacity planning:

In this topic, you should learn how your candidate planned the team’s resources and operations to achieve the revenue target they had. Efficient capacity planning is one of the most important factors to succeed in business. You should expect to hear a few key points when answering your questions. The points are:

  • Rev target
  • Quota attainment rate for each role
  • Ramped capacity vs. onboarding
  • ACV, opportunities, expansion targets
  • Gross retention, net retention consideration
  • Commission planning, acceleration incentives
  • On-boarding, ramp time, sales cycle length

Example of questions you can ask:

  1. What is your experience with sales forecasting and pipeline management, and how do you ensure accurate and timely reporting?
  2. Can you explain your approach to sales capacity planning, including how you assess market demand and sales team bandwidth?
  3. What are some common challenges you’ve encountered in sales capacity planning, and how have you overcome them?

Funnel analysis practices:

In this topic, you should learn how your candidate analyzed the sales funnel to identify weak points for improvement and better forecast the outcome. This is a data-driven work that RevOps or a data analyst can help with, but it is the VP of sales responsibility to ‘translate’ the data into actions in the sales operation. You should expect to hear a few key points when answering your questions. The points are:

  • Win/loss analysis
  • Opportunity qualification criteria
  • Inbound vs. outbound
  • Tooling beyond salesforce
  • Quota attainment & forecasting

Example of questions you can ask:

  1. What metrics do you use to measure sales performance, and how do you use them to inform decision-making?
  2. What metrics do you use to track sales performance, and how do you use those metrics to inform your strategy and decision-making?

GTM strategy from the ground up:

As your VP of sales is part of the GTM leadership team, you need to validate that the candidate understands the topic and can share examples of a successful GTM strategy. You should expect to hear a few key points when answering your questions. The points are:

  • Outbound vs. inbound motions
  • Tech & strategic channels and partners
  • Market segments, regions
  • Buyer persona analysis
  • Hunting ground / ‘feed the beast.’
  • Competition

Example of questions you can ask:

  1. How have you previously identified and pursued new business opportunities, and what strategies have you found most effective?
  2. How do you keep up with industry trends and adjust your sales strategy accordingly?
  3. Can you describe your experience developing and executing a GTM strategy for a B2B SaaS company?
  4. What factors do you consider when determining the optimal mix of sales channels for a given product or service?
  5. How do you evaluate the effectiveness of your GTM strategy, and what metrics do you use to track progress and make adjustments?

Deal management:

If your target market is Enterprise or mid-market, you need your sales team to know how to manage and win a deal. Unlike consumer and SMB segments, mostly done online or over the phone with a single buyer, more significant deals involve multiple parties. Legal, procurement, business, and privacy are just a few examples of teams you may need to engage with to close a $X00,000 deal. Competitive deals also require special skills to win. You should learn how your candidate experienced such situations in the past. You should expect to hear a few key points when answering your questions. The points are:

  • Opportunity validation
  • User vs. buyer persona
  • Mini org-chart
  • Wallet size
  • Value selling vs. feature selling
  • Legal and commercial teams engagement
  • Preparing offers and negotiating pricing
  • Competitive selling
  • RFP submission, presentation, and negotiation

Example of questions you can ask:

  1. Can you describe a time when you had to make a tough call or take a risk to close a deal, and how did you handle it?
  2. Can you give an example of a particularly challenging sales situation you faced, how you approached it, and the outcome?
  3. How do you approach deal management, and what steps do you take to ensure that deals move through the sales pipeline smoothly?
  4. How do you work with sales reps to identify potential roadblocks or deal-killers, and what strategies have you found most effective for overcoming these obstacles?
  5. How do you ensure all stakeholders (e.g., legal, finance) are appropriately engaged and aligned during the deal management process?

Cybersecurity Market:

Another area to cover in your interview is your specific market. As mentioned, at the early stages of ARR, you should value a candidate with experience in your market. Such expertise includes contacts with potential buyers, technical terms, product values, history, and competitors in the market. You should expect to hear a few key points when answering your questions. The points are:

Example of questions you can ask:

  1. Can you describe your experience selling B2B SaaS products in cybersecurity? What strategies have you found most effective in generating interest and closing deals?
  2. How would you build a sales team to sell a cybersecurity SaaS product? What roles would you prioritize, and how would you evaluate candidates?
  3. What are the biggest challenges in selling a cybersecurity SaaS product, and how do you plan to address those challenges?
  4. How would you approach selling a cybersecurity SaaS product to a new market or customer segment? What factors would you consider in determining whether to pursue a new market?
  5. Can you describe a time when you had to work with a customer to overcome objections related to data privacy concerns? How did you address those concerns and ultimately close the deal?
  6. How do you keep up with changes in the cybersecurity landscape and adjust your sales approach accordingly?

Tasks:

An interview process takes more than one call to decide if you have found the candidate you need. In between the calls/meetings, you can assign your candidate some tasks to complete. Here are a few examples you can use:

  1. Develop a sales plan for the next 6–12 months, including lead generation, target accounts, and projected revenue, per the 2023 business plan
  2. Onboarding plan for a new SDR/AE in the cyber security market.
  3. Sales plan for the next 6, 12, 18, and 24 months. Provide some data points so the plan will look as realistic as possible for your business. Example of metrics to share: your ACV, your ARR growth for the next 12 months, your ARR today, gross retention 90%, net retention 110%

Written by: Yuval Ben Itzhak

--

--

Evolution Equity Partners

International venture capital investor partnering with exceptional entrepreneurs to develop market leading cyber-security and enterprise software companies.