1. Pick one buyer and one hiring situation
Recruiting covers too much to interview everyone. Choose one person, such as an in-house technical recruiter at a 50 to 300 person startup, a solo agency recruiter, or a founder hiring their first five engineers. Then choose one situation, like filling senior engineering roles or high-volume hourly hiring. Every question you ask should point at that person in that moment.
2. Find recruiters where they already talk
Search LinkedIn for titles like "Technical Recruiter", "Talent Acquisition Partner", "Head of Talent" or "Recruiting Coordinator" and filter by company size. Read and join r/recruiting, r/recruitinghell (for the candidate side) and RecruitingDaily's community. Search Slack groups and LinkedIn for communities like RecOps Collective or local talent meetups. Founders hiring their first team show up in r/startups and Indie Hackers threads about hiring.
3. Send a short, honest ask
Ask for 20 minutes to learn, not to pitch. Example: "Hi Sam, I'm building a tool for in-house recruiters at startups. I'm not selling anything yet. Could I ask you 5 questions about how you sourced your last engineering hire? 20 minutes, any day this week." Send 10 to 15 of these a day and expect a fraction to reply.
4. Ask about the last real hire
Past behavior beats opinions. Start with: "Walk me through the last role you filled, from the day it opened to the day the offer was signed." Follow up with: "Where did the best candidate come from?", "Which step took the longest?" and "What did you do when the pipeline went dry?" Get dates, tools and numbers from their own story.
5. Dig into the tools and the workarounds
Ask: "What tools did you touch on that hire?" Expect answers like LinkedIn Recruiter, Greenhouse, Lever, Ashby, Gem or a spreadsheet. Then ask: "Where do you copy and paste between tools?" and "What do you track in a spreadsheet that your ATS should handle?" Workarounds show you where the pain is real enough to cost them time every week.
6. Find out who pays and how
A recruiter may love your tool and still not control the budget. Ask: "When you added your last recruiting tool, who approved it and how long did it take?" and "What do you pay for sourcing tools today, and who owns that line?" If they mention a Head of People, CFO or founder, ask who that person is and whether they would intro you.
7. Test commitment, not compliments
Never ask "Would you use this?" because everyone says yes. Close with: "If I built something that fixed the step you just described, could I show you in two weeks?" or "Would you pay to try it on your next open role?" A scheduled follow-up, an intro to their boss, or a pilot on a live req is a real signal. A polite "sounds cool" is not.
8. Write it down the same day and look for patterns
After each call, note the role they were hiring for, the slowest step, their tools, who owns the budget and their exact words about the pain. After 10 interviews, group the notes and see which problem came up the most and hurt the most. Hulby, an AI cofounder, finds and messages people like these daily so founders can spend their time on the calls themselves.
Mistakes to skip
- Pitching your product in the first five minutes instead of listening.
- Interviewing candidates or friends when your buyer is a recruiter or hiring manager.
- Asking hypothetical questions like "Would you use a tool that..." instead of asking about the last real hire.
- Ignoring who controls the budget and mistaking an enthusiastic user for a buyer.
Want this done for your recruiting tool, every day?
Hulby finds the people asking for what you built, writes every reply and email, and keeps you on it until they pay. Free to start.
Find my first customersQuestions
How many interviews do I need?
Aim for 15 to 20 with one type of buyer. Stop when you can predict their answers before they give them.
Should I talk to recruiters or hiring managers?
Talk to whoever feels the pain and whoever pays. At startups those are often different people, so try to reach both.
What if recruiters ignore my messages?
Make the ask smaller and more specific. Mention their actual open roles or a recent post, and offer to share what you learn from other recruiters.
When can I ask for money?
Once several people describe the same painful step in their own words. Offer a paid pilot on one live role and see who says yes.