Interviews, News

Introducing Ben Wright (and being pathologically obsessed)

Posted: 27 January 2023

We are very excited to welcome Ben as Crane’s latest Advisory Partner. Ben is London based and spends 100% of his time on the sales end of GTM with our portfolio companies. He’s already making a material impact.

Ben brings decades of experience in product management, marketing and sales in every conceivable GTM motion—large enterprise, mid-market, open source bottoms-up etc—coupled with having advised over 60 companies from Seed to Series A. Add to that his work training hundreds of sellers and sales leaders at the Sales Impact Academy. Bringing Ben on was a no-brainer. 

We sat down with Ben to talk more about his craft. Please enjoy.

Scott: What draws you to the earliest stages of startups?

Ben: I really enjoy this stage when there are so many unknowns in so many areas of a company’s GTM motion where I can help founders focus on their key problems and put meaningful plans in place to solve them. It’s a phase where we can add so much value, where we can set the foundations for world-class execution.

Scott: What are the biggest mistakes founders make in their initial GTM?

Ben: The two that I see most commonly:

  1. Very early stage – not narrowing down the Ideal Customer Profile, the ICP. It doesn’t have to be perfect, but you need to start placing some bets earlier than you feel ready for. You’ll inevitably sell some deals into sectors / geo’s / profiles of companies that end up not being right for you, which is a necessary part of getting closer to your real ICP. But as soon as you start seeing traction, you need to be pathological in looking for what’s common about those users or customers, and then concentrating just on them.
  2. Another big mistake is hiring a VP of Sales, or worse, a CRO, too early. A founder needs to run the GTM motion and team themselves to understand what works and what doesn’t for their combination of product and market. VPs of Sales are great at executing, but they’re rarely good at figuring out where the market is, or how to approach it. Only hire a VP Sales once you’ve narrowed down your ICP and worked out the whole sales process from lead gen to deal close.

Scott: What piece of advice do you share with founders who are still iterating towards PMF and only have a handful of customers?

Ben: Stay as close as you possibly can to customers and prospects. You should be talking to both every day. When I meet with founders who aren’t doing this, I often set a target number of customers for them to speak to. Doing so transforms their understanding of what their customers need and the value they get from the product. Founders need to understand everything about the pain they have, how this impacts them, their department and their business, how your solution takes this pain away, and what value is created by doing so. You need to understand this for both Users and for Buyers. I too often see the Buyers, the people who actually need to sign-off on the purchase of your product, getting left out of this conversation. 

For some help with that, I highly recommend reading The Mom Test by Rob Fitzpatrick and implementing his method of questioning.

Scott: How do founders know that they’ve figured out their GTM motion and that it’s time to scale?

Ben: When you’ve narrowed down your ICP, have a reasonably consistent flow of qualified leads and understand how to close deals, that’s the time to start hiring. A couple of examples of hires to make at that point below.

Top-of-funnel is always the hardest to get right, so the first hire I’d make is a generalist marketing manager, with strong content and digital marketing experience, who can build and run your inbound machine. A mistake I regularly see is companies hiring too late for this role.

From a sales perspective, if you’re blessed with inbound that is either in or pretty close to ICP, hire an SDR to have them qualify leads and book meetings for the founder who’s running GTM. 

Scott: That sounds like a lot of work for the founder to do before they start hiring.

Ben: Well, no one said building a tech company was easy! But, yes, it is a lot of work, and I have huge respect for founders who manage to cross this chaotic phase of growth to start building a more predictable revenue machine. No founder ever really has time to do this, but the reality is that those who go on to build great companies find a way to make this work. 

Why? Because if you don’t lay the foundations of a predictable GTM motion yourself, you won’t know what good looks like, what types of SDRs or AEs to hire, and what to look for in a good Sales Leader or what makes someone a good Sales Leader. You’ll also have no idea of how to measure and quantify success, because you have no idea of what is possible. Is 30 qualified opportunities and/or $200k a quarter in new business a great result or should you be aiming for 120 qualified opportunities and/or $600k per quarter? How would you even know?

Scott: What do the best early-stage AEs do that others don’t?

Ben: Building enough top-of-funnel, coupled with founder-like  pathological obsession to continuously improve the sales process. They’ll be constantly trying out new ways of attracting and talking to prospects about the pain they have and the impact of that pain. Top performing AEs in any company, but particularly early-stage, are great at Discovery. They’re deeply curious and genuinely interested in understanding as much as they can about their prospects’ worlds, and really unpacking the challenges they have and the value that can be created by solving them.

I’d recommend caution hiring AEs who only have big, well-known brands on their CVs, because they’ll never have experienced – and will likely struggle with – the chaos of early-stage. I’d also be careful hiring AEs who have had startup experience, but not for 5 years or more because the world of early-stage sales has changed a lot in that time. 

These first AEs are tough to hire, it’s more like you’re looking for people you want to partner with to help you through this difficult stage of growth. Not only are these AEs going to bring crucial new customers to the business, they’re also going to help you build out your sales playbook to make your sales machine more scalable. Think about the characteristics you’re looking for and optimise your hiring process to test for those rather than simply their experience. Things I look for are coachability, adaptability, resilience, mental agility, curiosity and a great work ethic.

Scott: What are the most important lessons you have learned from your career so far?

Ben: Well, that’s a pretty big question! My first answer will probably be a surprise, but I think kindness, in life in general, but particularly in business, is an under-appreciated value. Kindness doesn’t mean giving people an easy ride, it doesn’t mean not dealing with difficult decisions, and it certainly doesn’t mean not holding people to account for their actions or targets. But in every situation you find yourself in, there is always a kind and a not-kind way of dealing with it. 

If you have a sales rep who’s missing their target, is your first question ‘What the hell is going on?’ or is it ‘How can I help you?’. If you’ve just sat through or watched a recording of a terrible Discovery call, do you start your feedback by explaining all the things you think went wrong, or do you ask ‘How do you think that went?’ and really listen to what they have to say before giving your feedback on specific areas, with meaningful suggestions for how they can improve.

When it comes to early-stage, one of the best pieces of advice I was ever given (by an Ariba cofounder) – better to have a ‘B’ strategy ferociously executed than the endless planning that goes into the search for an ‘A’ strategy.

What he meant was that it’s far better to come up with a decent plan quickly, start executing, measure the results, improve the parts that are performing the worst and iterate your way to success. GTM is no different. 

And have fun!