My first sale wasn’t a repeatable software license sale — instead, I found success in selling a (temporary) consulting engagement with the scope of using my own prototype to train a new manager. Effectively becoming my product’s user#1 within their company.

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Reflecting back, four components were needed for this sales approach:

1. Correct target persona and problem.
2. Channel for appointment setting.
3. Establishing rapport through lingo and usability demo.
4. Offer to do a consulting engagement.

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1 / My first mistake assumed the end user for my product was the same person I needed to sell. And because I initially focused on the wrong persona, I highlighted the wrong problems which failed to establish rapport. No one explicitly said they weren’t interested, so I wasted many cycles iterating pointless sales messaging and seeding self-doubt. [A]

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After picking the correct target persona, my next mistake assumed people knew which problems were sufficiently hair-on-fire for them to justify new software. Parroting people’s words resulted in lackluster sales appointments. Instead, correctly guessing the root cause behind everyone’s problems became a “lightning bolt” moment in sessions. [B]

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2 / All the recommended tactics — inbound marketing, cold outreach, digital ads, thought leadership, leveraging past coworkers, warm introductions, hiring sales intern, paid interviews — are simply channels for setting a sales appointment. And turns out all channels are paid (through money, time spent writing content / engagement / follow-ups, or social capital).

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Appointment setting was the toughest work for me. Looking back, I should’ve made a decision on the interim cost I was willing to pay for an appointment during this 0→1 sales phase, and double-downed on the single most-convenient channel. [C]

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3 / I underestimated the importance of “insider club” lingo. Rapport required kicking off a sales appointment with certain questions, anecdotes, and commiserating. [D]

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For the demo, I didn’t have much luck with feature showcases / product tours. Instead, my usability testing format proved effective — 1-on-1 session where we created real data, did real user behavior, and completed a real usage path — as a way to preview my competence for a consulting engagement. [E]

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4 / Designing the right offer was the final piece of the 0→1 sales puzzle. Initially my offer was to sell software licenses, but this consistently received valid-yet-arbitrary objections. I suspect these days everyone has subconscious resistance to adding a new tool into their already bloated tech stack, let alone something experimental.

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Objections vanished after I pivoted my offer into a custom consulting engagement. I explained how I would become a fractional member of their team, use the product myself to solve their hair-on-fire problem, and train / hand-off to a permanent member of their team. [F]

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This framework is how I’ll tackle 0→1 sales for any future project. To troubleshoot a stuck sales flow, I’d recommend using this framework to figure out what’s preventing the founder from getting hired as a consultant.

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Takeaway

To get the first sale, do things that don’t scale such as offering a consulting engagement to become the first user of the product within the client’s company.

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Anecdotes

[A] Since I was building software which first-time managers use during their 1-on-1s, I initially targeted first-time managers for sales appointments. None of those appointments converted into a next step, so I pivoted to MBA students as future-managers seeking a promotion advantage and university faculty overseeing student researchers. Same story, so I pivoted to direct reports for peer-to-peer coaching. Same story, so I pivoted to HR Executives as a manager training tool and this too resulted in lackluster sales appointments. Finally I pivoted to Directors (at companies with 40-200 headcount, without a manager training program, and several younger managers as direct reports) and the appointments became night-and-day better.

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[B] The hair-on-fire problem which transformed my sales appointments: a department head’s top priority is constantly interrupted by low priorities escalating from new managers who struggle to make decisions in their 1-on-1s. However, the problems that people commonly voiced: “young managers have imposter syndrome”, “my managers shy away from difficult conversations”, “my new manager is struggling to transition from their individual contributor role”, “I frequently have to work late”.

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[C] My most convenient sales channel proved to be a paid user testing service which had SMB directors curious to discover and provide feedback on new tech. I initially used this service for iterative product development, but eventually realized I could likewise use it for iterative sales development.

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[D] If I were to create a script for my sales appointment, some lingo it would include:

• “How often do low priority things get escalated to you and interrupt the strategic work you want to do as dept head?”
• “Why do you think this happens — is it because new managers still try to wear their IC hat?”
• “Previously I worked at a place that coached CEOs of large tech companies and what you’re saying reminds me of [anonymized case study].”

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[E] Details of my usability testing format has been published @ https://typeshare.co/vlad/posts/the-secret-to-01-product-development-is-what-needs-to-happen-between-two-real-usability-sessions

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[F] The winning offer to directors was a remote training engagement — where I teach a new manager three decision-making templates (off-track goal, issue causing fear / anger, low motivation) in hourly 1-on-1 sessions, and then provide spot-coaching while shadowing 1-on-1s with their direct report, facilitated through my prototype web application — with the goal of decreasing how many low priorities get escalated to the director.