Documenting Early Stage Startup Sales: How the Deal Went Down

Sales is always hard. But sales at an early-stage startup is really hard. You’re always hustling. You have to be scrappy. You have zero resources and your growth targets would seem crazy to anyone who has never worked at a seed-stage software company (ask a salesperson in a big company if they ever had to grow revenue 10 to 20% every month!)

RELATED: Hiring your first B2B Saas Sales Rep

Important tasks like documenting sales processes so you can scale knowledge fall by the wayside. That “Sales Playbook” doc in Notion has zero blocks and is as dusty as the Peloton bike you bought last January. It’s obvious why: you’re moving fast, you’re short on resources, and no rep ever got paid commission by writing a sales playbook. Eventually you’re going to have to invest in this, but I have a hack you can use for now to make it work during this hypergrowth period. It’s called HTDWD.

What Is HTDWD?

How The Deal Went Down (HTDWD) is an email that a sales rep sends to the entire company for a “closed won” opportunity and to select team members (sales, product, founders) for “closed lost” opportunities. 

The structure is simple and shouldn’t take a rep more than 5-10 minutes to write. And I promise compliance will be higher than with all the other “administrative” tasks you ask of them. If you need help making it stick, it could be a condition of receiving their commission payment. Here’s what it looks like:

Email subject: “HTDWD: Client Name”

Email body:

  • What: Terms of the sale (e.g. “3 year contract: $25,000 implementation; $50,000 per year recurring; $175,000 TCV”)
  • How: 3 to 4 sentences on how you found the prospect (or how they found you), what their challenges (pain points) were, what parts of your product (or service) they found most valuable, and perhaps a little narrative about the sales process itself.
  • Why this is cool: What’s unique about this opportunity: Is it a record contract value? New vertical you’ve successfully sold into? A newly released feature that the client loved? Did you beat out a competitor in a bake-off?
  • Thank you: Selling is always a team endeavor. Shout out to other team members or departments that directly or indirectly helped you get the deal over the finish line. 

Celebrating Early Stage Sales Wins: A Win-Win

It’s imperative to always celebrate the wins. Signing up a new client is a team win. The salesperson should get recognition for getting the deal over the finish line and growing revenue. The product and engineering teams get to see tangible results from their hard work. Everybody should feel great when a client validates your hard work by investing to buy your product.

But here’s the real value in the HTDWD emails: these emails provide instant and typically actionable feedback for the entire team. If product and engineering teams see lots of HTDWD emails that highlight a popular feature, they know that they should invest further in that feature.

For existing sales reps it can get the competitive juices flowing – nothing is more motivating for a good salesperson than knowing a colleague is doing well or better than them. But more importantly, especially in the “How” and “Why” sections, they quickly learn what is currently resonating with prospects. For closed lost HTDWD emails, stakeholders get instant and actionable feedback on why deals are being lost, which can be used to address product gaps or weaknesses in the sales process.

Building Long-Term Sales Resources

Longer term, though, the emails are truly invaluable for ramping up new sales hires. Let’s be honest: 90% of seed-stage sales teams don’t have any written knowledge base that they can share with new sales reps. This is highly problematic. Expecting reps to wing it is a recipe for failure. This is where the HTDWD emails are magical. Imagine how much a new sales rep can learn by just reading 50 HTDWD emails on their first day! 

Ideally you’d have more sales resources to share with them (and you’ll have to get there eventually); but if that’s all you have they’ll have a 10x better chance of success than if they had nothing. For such a small investment after a deal has closed, these emails can yield massive dividends.

As former tech entrepreneurs, we’ve seen the impact that “small” changes like these can make to the growth of your business. Ready to get the guidance we wish we had back then? Talk to a partner at Scaleview Partners today.