1. Pick one agency type to interview
Proposals at a 3-person SEO shop look nothing like those at a 40-person paid media agency. Start with small agencies of 2 to 15 people where the founder or head of growth writes proposals personally. Pick one niche, like Shopify ecommerce agencies or B2B SaaS content agencies, so answers are comparable.
2. Find agency owners where they already talk
Search LinkedIn for "agency owner" or "founder" plus "digital marketing agency", filtered to 2-50 employees. Read r/agency and r/digital_marketing for posts about proposals, scoping and pricing. Look at the Agency Hackers, Bureau of Digital, and Modern Agency Owner communities, plus Facebook groups for agency owners. Search X for "proposal" "agency" "hate writing".
3. Send a short, honest ask
Ask for advice, not a sale. Example: "Hi Sam, I'm building a tool to help small agencies write proposals faster. I'm not selling anything yet. Could I ask you 5 questions about how you write proposals today? 15 minutes, any day this week." Send 20 a day and expect a few yeses.
4. Ask about the last proposal, not proposals in general
Concrete past events give honest answers. Ask: "Walk me through the last proposal you sent. Who asked for it, who wrote it, and how long did it take?" Then: "What did you copy from older proposals?" and "What part took the longest: scope, pricing, case studies, or the writing?"
5. Dig into what it costs them
Find out if this pain is worth paying for. Ask: "How many proposals did you send last month, and how many closed?" "What happened to the ones that didn't close?" "Have you ever skipped or delayed a proposal because you were too busy?" and "Who else reviews it before it goes out?"
6. Ask what they already tried
Ask: "What tools do you use now? PandaDoc, Proposify, Better Proposals, Google Docs, ChatGPT?" Then: "What made you start or stop using it?" and "What do you pay for it?" If they already pasted briefs into ChatGPT, ask what was wrong with the output. That gap is your product.
7. Close with a real next step
End by testing commitment. Ask: "Next time you get a proposal request, could I write the first draft for you with my tool and you tell me what's wrong?" Someone who sends you a real brief is a lead. Someone who says "sounds cool, let me know" is not. Log every answer in one spreadsheet.
8. Repeat daily until patterns show
Do 10 to 15 interviews before changing your product, then look for the same complaint repeated in their words. Use those exact phrases in your landing page and outreach. Hulby, an AI cofounder, can find agency owners to contact and draft these messages for you each day.
Mistakes to skip
- Pitching your AI features in the first five minutes instead of listening.
- Asking "Would you use this?" when people always say yes to be polite.
- Interviewing freelancers, solo consultants and big agencies all at once, so no pattern appears.
- Ending the call without asking for a real proposal brief to draft.
Want this done for your AI proposal writer for marketing agencies, 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?
Start with 10 to 15 in one agency niche. Stop when you keep hearing the same problems.
Who exactly should I talk to?
Whoever writes the proposals. At small agencies that is the founder, managing director or head of growth.
Should I show a demo?
Not in the first interview. Learn their process first, then offer to draft a real proposal as a follow-up.
What if nobody replies?
Make the ask shorter and more specific, mention their agency's niche, and send more. Low reply rates are normal at the start.