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High-Impact Discovery Questions for Selling to Heads of Talent in EdTech

Summary:

Uncover unique talent acquisition and development challenges, align on scaling growth and innovation, and accelerate deal qualification with questions tailored for talent leaders in the EdTech sector.

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If you sell HR Tech or Enablement tools to Heads of Talent at EdTech companies, discovery is where the deal is won or lost. The right questions help surface business pain, align on value, and drive urgency.

30 Discovery Questions for Heads of Talent in EdTech (HR Tech)

A. Getting Started & Strategic Priorities

  1. What are your top 2-3 talent-related priorities for the next 12-18 months, considering the rapid growth and innovation in EdTech?
  2. What prompted your interest in exploring new HR Tech solutions specifically for talent management at this time?
  3. How does your talent strategy support the company's overall goals for product development, market expansion, and user acquisition?
  4. What are the key initiatives your talent team is currently focused on to attract and retain top-tier educators, technologists, and content creators?
  5. How would you describe the current state of your talent acquisition and talent development technology infrastructure?

B. Current HR Landscape & Challenges

  1. What are the biggest challenges you're facing in sourcing and hiring specialized talent (e.g., curriculum designers, AI engineers, instructional designers) in the competitive EdTech market?
  2. How effectively are you able to onboard new hires, particularly remote or globally distributed talent, to ensure they become productive quickly?
  3. What are the primary pain points your talent team experiences with your current Applicant Tracking System (ATS) or manual recruitment processes?
  4. How do you currently identify and address skill gaps within your existing workforce to keep pace with evolving educational technology trends?
  5. What challenges do you face in retaining key talent, given the high demand for EdTech professionals?
  6. How are you currently managing performance reviews and career development paths for your employees?
  7. How effectively are you able to utilize talent data to predict future hiring needs or identify retention risks?
  8. What are the biggest hurdles in building a diverse and inclusive workforce that reflects your user base?
  9. How do you ensure your employer brand effectively attracts the right caliber of talent in a crowded market?

C. Future Vision & Goals

  1. If you could improve one aspect of your talent lifecycle (e.g., recruiting, onboarding, development, retention) in the next year, what would it be and why?
  2. What would a truly integrated talent management system enable your team to achieve that you can't today?
  3. What does an ideal candidate experience look like for your EdTech company, from application to offer acceptance?
  4. How would enhanced talent analytics and insights impact your ability to make strategic workforce decisions?
  5. What kind of impact are you looking for on time-to-hire or employee engagement from new HR Tech?

D. Quantifying Impact & Value

  1. What's the estimated cost of your current time-to-fill for critical roles, or the impact of high turnover on product development cycles?
  2. How much manual effort or administrative time is currently spent by your talent acquisition team on tasks that could potentially be automated?
  3. What is the financial impact of a prolonged hiring process or a poor onboarding experience on new hire productivity?
  4. How does a lack of clear career development paths impact employee morale or retention rates?
  5. What would a X% improvement in talent retention or a Y% reduction in time-to-hire mean for your company's growth trajectory?

E. Understanding the Buying Process

  1. Who else within the EdTech organization (e.g., CTO, Product Head, CEO, Finance) would be involved in evaluating a new HR Tech solution for talent?
  2. What are the key criteria your organization uses to evaluate new technology investments, especially those impacting human capital?

F. Budget & Investment

  1. Do you have a specific budget allocated for talent technology improvements this fiscal year, or is this something that would need to be built into next year's planning?

G. Timeline & Drivers

  1. What's your ideal timeline for implementing a new HR Tech solution, and what's driving that timeframe?

H. Exploring Alternatives

  1. Have you explored other HR Tech solutions for talent management in the past, or are you currently evaluating any alternatives?

I. Implementation & Long-Term Success

  1. What does a successful implementation of a new HR Tech solution look like for your organization, beyond jus going live?

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How Pepsales AI Helps

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Pepsales AI helps sales teams ask the right questions, faster. It delivers intelligent, role-specific, and industry-aware discovery questions in real time tailored to the context of each deal.

What it delivers:

  • A library of proven questions per industry, persona, and product
  • Smart prompts that adapt to buyer role, objections, and stage
  • Embedded coaching and insights to guide better conversations
  • Automation of discovery prep, no more guesswork

Whether you’re prepping for a demo or coaching new reps, Pepsales AI ensures every conversation starts strong and gets to the real need, fast.

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