Have you ever joined a company, impressed by how amazing everything seemed during the hiring process, only to discover a completely different reality once you started? If you've been working for more than 8 years, I'd wager that it happened at least once in your career.
But don't fret. Here are 90 questions for you to probe the hell out of your potential next gig and make sure you understand exactly what you're getting into.
Financials:
- Can you provide or review the latest P&L?
- Are there any outstanding debt or other liabilities present in the business, if so, how does that impact the P&L?
- What is the current burn rate, and how has it been trending?
- What is the company's current cash runway?
- What are the primary revenue streams? Are there any plans to diversify?
- What percentage of revenue is recurring versus one-time?
- What are current Gross Margins? Are they holding to expectations?
- Are there infrastructure commitments impacting Margins & COGS?
- Are those going to plan or are they overrun?
- Can you provide 2 years of quarterly bookings and revenue trending data?
- What is the current year's bookings and revenue plan?
- How is current year performance tracking?
- Is the company ahead or behind quarterly performance targets?
- Is there pipeline sufficiency to meet the FY bookings and revenue plan?
Customer Base:
- How many current customers do you have?
- How are customers segmented (e.g., by industry, size, usage)?
- What is the average CAC?
- What is the composition of the customer base (% or actual #’s) by Market Segment and Geography?
- What is the current Gross Renewal Rate?
- Can you provide 2 years of GRR performance?
- What is the Net Retention Rate?
- Can you provide 2 years of NRR performance?
- What is the Net Promoter Score?
- Can you provide 2 years of NPS performance?
- What is the average Customer Lifetime Value?
- Are there any customers that contribute a significant portion of the company’s revenue?
- IE. 20% of the customers make up 80% of the revenue?
- Are you measuring expansion revenue by individual customers? If so, what % of customers have expanded?
Competitive Landscape:
- How does the company position itself against competitors?
- Can you provide a recent SWOT analysis?
- How is competitive intelligence gathered and used?
Marketing:
- What is the current marketing strategy?
- What is the ROI on the different marketing channels?
- What % of revenue is the marketing budget?
- What is the split of marketing spend (Digital/Social, Brand, Inbound, Outbound, Tradeshows)
- What percentage of pipeline is marketing delivering? Is that on target to expectations?
- What is the MQL to SQL ratio?
- What are the primary customer acquisition channels being utilized by marketing?
- What is our target audience and the buyer personas we focus on?
- What are the primary KPI’s marketing is measuring?
- What technologies and tools are in the marketing stack?
- How is the marketing team collaborating with Sales today? (Annual marketing plan/Quarterly marketing plan)
- Are there any upcoming signature marketing campaigns to drive brand awareness?
Sales Teams:
- What is the current organizational structure/chart for the sales team?
- What is their geographical organization?
- How many AE’s are in the org?
- How are sales targets set and adjusted?
- What is the target productivity for tenured AE’s?
- What is the composition of AE’s between tenured, ramping and < 6 months?
- Do you have two years of AE attainment data?
- What is the FY quota over assignment percentage?
- What is the compensation plan?
- What is the AE OTE to Quota ratio (ie. Target average quota / OTE)?
- What is the Average Deal Size? some text
- Is there two years of trend data?
- What is the Average Sales Cycle? some text
- Is there two years of trend data?
- What is the average number of deals closed by AE in a quarter?
- What is the hiring plan for FY?
- Are you on target for planned hires?
- How many open backfills are there? How long have they been open? Why are they still open?
- Is there a new hire field training for sales?
- What sales methodology is currently being used?
- Is there a documented customer engagement process & methodology? If yes, is that aligned in the CRM?
- Is there a current net new pipeline generation target? If yes, is it being met?
- What is the current Close Ratio against all pipeline?
- What technologies and tools are in the sales stack?
- Is there a Sales/Company Kickoff and Top Performers Club plan?
SE Team:
- What is the current organizational structure/chart for the SE team?
- How many SE’s are in the org?
- What is their compensation plan?
- How do SEs collaborate with the sales team during the sales process?
- How are SE’s measured for performance outside of compensation plans?
- What % of the Sales conversation do they usually own?
- What is the FY SE hiring plan?
- Are you on target for planned hires?
- How many open backfills are there? How long have they been open? Why are they still open?
Customer Success Teams:
- What is the current organizational structure/chart for the Customer Success team?
- How many CSM’s are in the org?
- What is their compensation plan?
- What is the process for managing renewals and identifying at-risk customers?
- Is there a documented customer engagement process & methodology? If yes, is that aligned in the CRM?
- Are there programs in place to promote customer advocacy and referenceability?
Product:
- Can you share the product roadmap and any major upcoming releases?
- How is customer feedback integrated into the product development process?
- What tools and metrics are used to track product usage and engagement?
- How are compliance and risk management handled?
Company Culture:
- What are the core values of the company?
- What is the current employee retention rate? Are there any notable trends?
- What diversity, equity, and inclusion initiatives are in place?
Go get them!
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