BOOTSTRAPPING ★ 11 upvotes 2019

Ask HN: Sales advice for a bootstrapping founder needed

The Founder's Submission

Direct narrative and submission text authored by @soneca on Hacker News:

I am a solo founder bootstrapping (as a side-project) a SaaS web app for team managers at mid-sized companies.

It is a note-taking app exclusively for 1:1 meetings [0]. It allows to better register meeting notes, long-term goals and short-term commitments (the last two are shareable with the team members for better accountability).

I have a fundamental doubt in my sales strategy: should I target the individual managers that would use my product themselves or should I target HR executives that could buy my product and implement it to all managers at the company at once?

I am at a very early stage, with 2 paying customers that hired it themselves for individual use; and 5 colleagues at my day-job employer on a free-trial before I try to sell it to our HR director for the whole company.

The pros for individual managers: shorter sales cycles; direct feedback on the product; easier to find the contacts; more people to contact (guessing here).

The pros for HR executives: more revenue per sale; if successful - I assume - more retention.

[0] https://www.oneonemeeting.com

Retrospective Overview & Key Insights

Distilled analysis of the business dynamics, operational challenges, and strategic takeaways:

Published in 2019, this chronicle by @soneca details the mechanics of building a profitable, self-funded business without venture backing.

Core Principles for Independent Builders:
1
Charging customers from day one acts as the ultimate filter for building software that solves genuine, high-urgency problems.
2
Keeping fixed overhead low and leveraging lean infrastructure allows founders to stay alive until market tailwinds kick in.
3
Small, repetitive improvements in customer retention and conversion rates yield massive returns over multi-year horizons.
Community Debate Themes:

The community focused on B2B customer acquisition channels, cold email vs SEO distribution, and balancing full-time employment with side-project development.

Community Discussions & Critical Reviews

High-signal perspectives, counter-arguments, and peer founder insights debated on Hacker News (12 total discussions):

RS @rsweeney21 Peer Contributor

I bootstrapped my current company to several million in revenue. Both are valid strategies, but require very different skills and tactics. If you have another source of income right now, I would implement a product driven growth strategy [0].

Give your product away for free for individuals. You'll remove all barriers to adoption and be able to grow your user base quickly. If your product is valuable, your product will grow virally inside a company as managers see other managers using it. Once you have a few managers at Company X using your product, that's when you call up the HR department and offer them a paid company subscription for features like teams/user management, single sign on, sharing one on one results up the chain, whatever. Your users at the company become your champions. You can also provide an upgrade path in app if companies decide they want access to those features before you realize it.

Use a tool like Intercom to track how many users you have within a company.

It will delay revenue for a while, but give you a chance to refine the product from user feedback. It's also a much more scalable sales/marketing strategy for solo founders.

[0] https://expand.openviewpartners.com/your-product-is-your-go-to-market-strategy-heres-why-b1881c0c521 https://mattermark.com/product-led-approach-sales/

MC @mchannon Peer Contributor

Snap up oneononemeeting.com and redirect it (or redirect your current to that one). I couldn't get your name right and I'd probably be typical.

Firm up the pricing a little better. I get that "enterprise" would want to negotiate a deal, but nothing gives a prospective customer the middle finger like "call for price". If you know what your product is worth, tell me.

Anchor with an overpriced/not-much-nicer top selection, because that'll draw people to your ideal mid offering and away from the free.

To answer your doubt, make both pricing options.

JA @jakequist Peer Contributor

I think @rsweeney nailed it. Your product is one that _should_ sell itself.

You only needs a complicated sales cycle if you're selling deep infrastructure or where high degrees of trust are required. But in your case, users can look at your website and immediately determine if they need your product and how much they're willing to trust you.

Re: your product --- It looks super cool. It's not something I need at this point in my career, but maybe down the road. Good luck!

CV @cvolzer3 Peer Contributor

Target the end users with cheap/free/trials to gain significant traction then make your pitch to executives. By then, you already have all the evidence you need to make the sell.

RE @realty_geek Peer Contributor

Something like this? https://amazemeet.com/

HISTORICAL ERA Cloud & Mobile Era (2014–2019)
COMMUNITY SCORE ★ 11 points
TOTAL DISCUSSIONS 12 comments
TOPICS & TECH STACK: