Selling ahead

Without landing in jail

👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.

Being an entrepreneur for 30 years has given me SO many sleepless nights – getting down to one week’s worth of cash runway, laying off lots of great people, parting ways with or demoting co-founders. The list goes on.

But for about a year at FirstUp, I would often wake up at 4 a.m. in a blind panic.

We had raised and spent $30M, pulled off our last pivot (the one that worked), and now had to deliver on our vision for “mobile workforce communications.” I was selling that vision, hard, to employees, clients, and the board.

But our software platform just didn’t live up to my promise. And that gap would wake me like a panic alarm clock. I felt like if the board asked me to demo the platform at a board meeting, I’d be exposed as either delusional – or worse, a fraud.

We were trying really hard – but the reality was that my engineering team was just not up to the task. I was part in denial, part reluctant to spend more time and money to rebuild the engineering team.

The fact is: You should always be selling ahead. If you don’t, you’ll struggle to compete – all customers (consumers and enterprise) want to buy the future.

But selling too far ahead can get you in trouble. So here’s my guide to selling ahead in a smart way, born from too many sleepless nights.

– Greg

Managing the risk of selling ahead

There are two big reasons to sell ahead:

1. Your vision is more compelling than your current offering. The whole reason you’re selling ahead is because you think what you could build is better than what you have built. An offering that doesn’t exist yet is more competitive precisely because no one (including you) has built it.

2. You want to assess demand before you invest to build something. You can’t get real demand signals with a hypothetical product. If you say, “If we had [x], would you buy it?”, you won’t get useful feedback (most clients say, “sure” or “that sounds interesting” and then fail to follow through). You need an actual (pretend) product on the table to assess their level of commitment before you invest precious time and dollars.

But how far to sell ahead is a judgment call based on a continuum of risk.

On one end, you have offerings that will exist by the promised deadline – they’re already on your product roadmap with a date. Those are incredibly low-risk … but also probably not ambitious enough to excite anyone. Talking about these is not “selling ahead.”

Great leaders are closer to the right side of the continuum – they talk about offerings that don’t exist, but are based on core assumptions they have confidence in.

The key is to be bold without going into the danger zone. That’s where you get promises like Theranos – tech that can’t exist without a massive technological breakthrough, and yet is being written into contracts. With FirstUp, I was edging too close to the danger zone. Hence the sleepless nights.

Here’s an example from Section on the difference between “danger zone” and “sweet spot.”

In November 2023, Taylor and I started working on ProfAI – an AI-powered learning platform. After a year, we didn’t have a good enough user experience and hadn’t even proven that AI could do what we needed. If I’d been signing contracts for ProfAI, we would have been screwed.

But earlier this year, our new product/eng team had a breakthrough and proved that AI could power a personalized and high-quality coaching experience. So I started putting ProfAI into enterprise contracts and setting up demos for clients.

To the internal team, this shift probably seemed abrupt, since we still didn’t have a finished prototype. We still have a lot of work to do. But now it’s about executing well (still hard) – NOT making an unproven technical breakthrough.

The best leaders are good at selling ahead because when someone says, “Great – I’ll buy it,” they figure out how to make the outcome happen in time.

It boils down to – if we had to deliver this product in a X timeframe, could we?

My rules for selling ahead

Here’s my playbook after too many sleepless nights:

• Sell anywhere from 3-12 months ahead, depending on the complexity of the deliverable (Sam Altman is clearly selling years ahead for AGI … maybe he is a good sleeper)

• Be intellectually honest in your own assessment of your team’s ability to pull it off – can they do it or at least get close?

• Understand the 1-3 things (not 10) that need to go right/work to deliver on the promise – and never lose sight of those milestones

• Pay attention to your own level of discomfort – too little and you’re not being ambitious enough; too much, over 6+ months, isn’t sustainable – for you or the team.

Our advice

It’s easy to get frustrated when your CEO or head of sales starts selling a product you know doesn’t exist.

You probably start thinking, “Do they even know how much work that would be? Do they have any idea what’s on the roadmap? Are they completely delusional?”

Not completely – but a little bit delusional, yes.

Good leaders participate in this optimism rather than get freaked out by it. Let go of your baggage – usually it’s being on the hook to deliver the product – and instead think “what could we do if we had more time, money, people, etc.?” Act like AI; hallucinate for a bit.

Great leaders sell ahead their own part of the business. They paint an ambitious vision of what their team could deliver, and if others buy into it, they figure out how to make that happen. People want to work for and with other people that show them the future. Selling ahead is one way to do that.

Have a great week,

Greg & Taylor