Scaling to $30m in revenues (part 2 — product)

Yesterday I started jotting down a few thoughts in response to a question I saw on Quora asking, “what are the most typical challenges high growth companies face?”.

I kicked off with talent; because, simply put — a startup is only as good as the people within it. Failing to attract and retain the ‘right’ people, severely increases the chance of failure.

In this post I wanted to talk about product strategy and roadmaps.

I should caveat this with the fact that startups are, by nature, pretty unique — and that applies to the problems they are solving. So this isn’t a catch-all nor will it apply to every startup, I’m talking from the perspective of the businesses I have built, advised and invested in over the past twelve years. For example; a digital advertising network, a photo & video sharing app, a Groupon competitor in South Korea, an online learning platform, a cloud storage business, and a few online retailers.

I should also provide some context, this post is regarding startups that are starting to gain some traction. They’ll perhaps just have raised a sizeable funding round. The shareholder base will be growing, and they will be starting to become more silo’d in terms of specific functions in the business (operations, HR, product, marketing, etc.).

At this stage of the business it’s reasonably easy to set the north star for the business; most team members should understand the fundamental problem they are solving.

Likewise the board and new investors should understand the direction the business is heading, as well as (rough) goals in terms of users, market share and revenue. The real challenge is in moving these rough goals into tangible objectives, linked to a financial model — upon which performance reviews are based.

Over the past few years I’ve tried many different approaches; including Google’s famous OKR system; and trust me, to experiment properly is no small feat, in terms of explaining the system that is being adopted to the whole team, implementing it and giving it enough time to succeed or fail. I should also note the following is just my approach, not necessarily correct, but just what worked for me.

I would usually start with a 3 year plan. I draft a press release (which will never go public or see the light of day beyond the team) describing what the desired outcome is. It will include how we got there, key hires, key decisions, etc. Similar to what Jeff Bezos asks his product leaders to do at Amazon. The following is a quote from Mike George, VP of Echo, providing a little more context:

“We have a thing called ‘working backwards.’ The first thing we do is we write a press release, ignoring every technical thing we can’t do for now. It’s our aspirations. We also write FAQs where we identify every question we would receive as if we issued the press release. We answer the question in aspirational ways too, ignoring, for the moment, the technical hurdles.”

And yes, of course the world could end tomorrow and there are a million variables to consider, but I firmly believe this exercise helps put a stake in the ground — it helps you “come up for air” and ensure you’re heading in the right direction, and staying close to your vision (because at this stage you’ll have a million people advising on what direction the business should be heading). It’s all to easy to get trapped with the minutiae of managing a startup day-to-day, dedicating your time to fire fighting, but it is well worth blocking out a day or two to the birds eye view.

Once I have reaffirmed the 3 year plan, and discussed it in an open and collaborative forum with members of the management team and board, it’s then time to start to pair it back to a tangible roadmap (coving product, hiring and operations).

At this stage I’d usually start working on a draft Trello board — simply because it allows you to quickly drag and drop categorised boxes around. I’ll also keep it quite rough at this stage (and perhaps only keep it to myself — for now whilst I clarify my thoughts, or work on it alongside my co-founder / COO). I’ll put months along the top starting from this month and adding later months out right (you can also use quarters). To the left of the month columns I will have the backlog. Based upon the financial results we are expecting / operational plan I’ll place hires in boxes and place them in the respective month we hope they will start.

In parallel with the creation of the goal orientated product roadmap, I’ll also start working on the financial model, starting with assumptions — backed up with all of the data that has been collected over the past year or two of operations (p.s. you’ll most likely already have a financial model that you used to pitch to investors — that’s why it’s useful to do this exercise prior to funding, because it’s a difficult story to start having to explain a different financial model straight after closing).

Next, once the above has been refined and is in a coherent format, it’s worth sharing with the board and the rest of the senior management team to get their input (in fact they will most likely have been involved prior to this and throughout the step above).

Once you have buy-in from the board and senior management team, it’s time to get the team together (probably at a TGIF or a specific strategy meeting) and explain the high level approach, the high level goals, and how they will translate and impact their goals / targets / responsibilities.

Then it’s up to the function heads (head of product, talent, operations, etc.) to manage the backlog items that pertain to them. Also at this stage (once the roadmap is at a functional level), I tend to agree with Roman Pichler regarding goal-oriented product roadmaps. These focus on goals or objectives like acquiring customers, increasing engagement, and removing technical debt. Especially important if your product is young, is experiencing significant change or that the market is dynamic with new competitors or technologies introducing change.

Okay, back to the roadmap — some other tips that I have picked up:

  1. Tell a coherent story — the roadmap should be realistic and tell the story of your product over the next few years. It shouldn’t oversell, and it should be matched with the audience (team, investors, etc). Each release should build on the previous one and move you closer towards your vision.
  2. Keep it simple (to start with) — resist the temptation of adding too many details to your roadmap. Keep your roadmap simple and easy to understand. Capture what really matters and leave out the rest by focusing on the goals.
  3. Build in unison with the financial model — coupled with #2, by building the financial model at the same time, it will keep everything aligned and make dialogue and updates to the shareholders easier.
  4. Have a process the whole team understands (product backlog, grooming, etc.) — the whole team should be able to contribute to the product backlog, you should have a defined process and software. E.g. I used to go through the backlog with my co-founder each week. When people see their ideas being discussed, it makes them part of the family and they’ll work so much harder.
  5. Roadmap should be accessible (trello board for team members) — don’t really need to elaborate on this one. It needs to be accessible by everyone (on the team) anywhere. They should be able to see it progressing, living, changing and know why.
  6. Say NO, a lot — read this.
  7. Use dates (some people prefer not too) — you’ll find yourself automatically trying to add dates, even if you end up using release versions etc. Everyone thinks in dates — use them.
  8. Make sure the roadmap is measurable — state targets

Sorry that the post stops quite abruptly. I gave myself 30 mins to write this post, and now have to jump to a meeting. I’ll come back this evening and edit / tidy up a little more. Just pushing it out there so I get something out there.

Next, I’d say Founders & CEOs typically struggle with marketing. I’ll jot down a few thoughts in a follow-up post.

Thanks so much for taking the time to read this, and if you have any questions, be sure to reach out on Twitter. If you enjoyed it please do share and recommend.

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