Just recently, a woman was in a panic that the 7500 tabs she had open on Firefox browser were lost when her browser crashed. It’s pretty easy to cast stones there, but who amongst us doesn’t have a few too many comfort tabs/windows open?
At Notion, there’s a massive amount of effort and resource put into helping its portfolio founders and execs learn and thrive–and I know hundreds of links are pinged across emails and Slack and WhatsApp, to be opened and probably left idle to ‘not forget’. Or when you do need a reminder on best practices, you forgot where you heard it. Was it that woman on LinkedIn? Was it someone’s blog? Oh shoot, what were the best keywords to use to search to find it?
So, in an effort to spare some weary techdesk from that old ‘have you rebooted your computer lately?’ chestnut, and let you close some tabs (and to have just one link to remember), I introduce the ‘everything’ post.
I’m going to summarise briefly here some of the how-to posts I’ve written so you have just one place to have everything, and will update this accordingly (with the kind accommodation of Seb, the Head of Digital Marketing).
Right. So you’ve started a company, raised a bit of funding, have a product and now need to get people to pay you for it. The person who should be doing the initial conversations and sales, is you. You need to hear feedback from the market, you need to bring your vision to the field, you need to understand the challenges from the people who you want to pay you. How do you do this if you’ve never been a salesperson? Start by documenting everything so you can figure out your own correct Sales Process. This is now easier than ever, with AI notetakers able to transcribe meetings, pull themes, etc. The key to going from Product-Market Fit to Go-To-Market Fit is creating something repeatable. Please do not start scaling before you have PMF and GTMF. I always say sales is a blend of art and science. Too much art and each deal is recreated from scratch, takes too long and is too resource/financially heavy to land and then support. Too much science at the beginning and you might miss key nuggets that unlock greater sales; you’re selling to people, not robots. (yet). Learn how to document everything so when you do hire your first salesperson you’re setting them up for success.
It’s really easy in the beginning to get excited by anyone who wants to give us money. It’s then really hard to have to service 3 wildly different customers with different problems, different expectations and different product requirements. In the beginning, you have to be relentlessly focused on who your Ideal Customer Profile (ICP) is and how you solve that challenge. What you say no to is just as critical to your growth as what you say yes to. Say no to hiring extremely senior enterprise salespeople if you don’t know if your ICP is enterprise or midmarket yet. Say no to prospects who you know you won’t be able to properly support yet. Say no to throwing bodies at a problem instead of really understanding what the customer needs?
You have a few customers that you’ve closed and hopefully have either renewed, or are clearly showing that they are finding value from your solution. There is a clear ICP, you understand the pain you’re solving for and you’ve found that there are clear patterns and repeatability. Time to hire a salesperson or two! You’ve just spent probably a few years thinking about this company, living this company, spending a massive part of your waking hours focused on the company. Please put the right amount of effort into planning how you’re going to hire and onboard your new salesrep. Having a nice chat with someone who seems hungry isn’t the same as really thinking through what your company needs, how you can ask the right questions, and how you can make sure this person is successful. And you’re probably going to be the sales leader for now, as well as sales engineer.
Congratulations! You’ve learned first-hand the challenge of managing ambitious sales execs, and see that it really is a full time role to properly manage, coach, support them, and be a contributing part of the exec team, as well as feedback to the product, marketing, and exec teams so you look like a hero when presenting to the board. Or at least you sound credible and the numbers you promise aren’t orders of magnitude out from what you deliver. It’s almost a trope that the first sales leader comes in bright-eyed and raring to go and fizzles out. Yet what nobody talks about is that mostly it’s not their fault, they were never set up for success in the first place. Let’s start bucking that trend and making sure you’re happy, they’re successful and your GTM team thrives.
Part of GTM-fit is repeatability, and you can’t scale without that. You also can’t scale without serious planning, and cross-functional alignment and having the right process in to adjust as necessary before things get dire. What does a great operating cadence look like, and what should your team be doing on a daily/weekly/quarterly/annual basis to ensure success?
Once you have multiple sales execs, you’re essentially giving them their own franchise–they represent your business to their territory and have use of the shared resource functions of the rest of the business. However, having them operate in a vacuum without the full understanding of the rest of the business is a recipe for disaster. How many deals have been sold that include functionality that isn’t even on a roadmap? How frustrated has your product team been by hearing one thing from a rep and a totally different thing from the Customer Success team? A well-run QBR gives your sales team a chance to show that they have mastery and forethought over their territory and what will bring success—or an early warning that it’s going sideways.
Especially now, selling is tough. Demand generation is harder than ever, you have lots of competition (including do nothing), and it takes more focus to ensure that you are proving value to the customer because budgets are shifting. For those must-win accounts are you planning ahead or doing post-mortems? Account plans used to be extraordinarily tedious, and stale before that tab was even closed. There are lots of new tech companies out there helping automate some of this, making the real point of an account plan–the synthesis and orchestration and resourcing the fun part!
If a deal is important enough that it appears on the Board deck, or is critical to making your number or logo acquisition, it deserves deep thought on its own with a Deal Review. When you pull people from across the business to give their unvarnished viewpoint and ideas, it’s incredible how the ‘hope’ factor goes out the window and a solid next-steps plan comes into play. Learn how to structure a deal review session that is proactive and helpful rather than just confirming the close date and amount in your CRM is correct.
Even the greatest salesperson might go through rough patches, or get off to a slow start. But how do you know if it’s a skill/will issue or if there is something deeper at play? Letting your superstars just get on with it, not leaning in to help them often counterintuitively just leads them to leave. And we all know a rotten apple spoils the bunch….can you really afford to spend time and resources on someone who will never get there? Is it kinder to everyone to cut ties? Use this framework as a start to ensure you invest in the right people, and know where you need to cut.
It’s no secret that the average tenure of a CRO is less than 2 years. Yes, there are exceptions, but the person you hire at $3M in sales is probably not the same person you need at $100M, so please quit telling recruiters you need someone to take you from there to that. How much are you willing to invest in them, and what happens if they scale the business even faster than planned? It’s a conversation nobody likes having, but having forethought to structure something well ahead sets everyone up for a shared vision. What do the different stages of the company even need? From $0-$1M is a whole different ballgame than $10M-$30M. Don’t get caught out making changes too late.
With the rate of change that every part of an organisation is facing, what worked 12 months ago probably needs some tweaking. The good news is that it's never been easier to access the data you need to figure out where the weak points are. The bad news is that change takes time and effort and you can’t change everything at once, nor should you. Luckily others have trodden the same challenged path you have and are more than willing to share what worked for them—the little adaptations that ensured they were still headed on the right path even in spite of challenging market conditions.
Lots more articles to come this year, and please tell me what else you want to hear about.
Growing a business isn’t for the faint hearted, but there’s lots of resources available to help, if only you could just remember which tab that was.