From $10m to $100m in ARR with Nick Cheetham, CRO, Currencycloud


  • Identify your most valuable segments and if insufficiently large to meet your goals, target adjacent segments methodically, just like pins in a bowling alley
  • Explore best practices across the entire customer lifecycle: just winning a client is a necessary but insufficient part of the job
  • If you are rolling out Pods, invest in training the team on the behaviours that align with autonomy, accountability and high performance - built on trust
  • Maximise growth through an obsession with marginal gains across the bowtie
  • Don’t go it alone, get perspectives from those that have been there and done it

Who’s the customer?

As a company comes out of the early founder-led stage, into what Notion calls BUILD, the very first steps, as far as I’m concerned, are understanding your value (as perceived by your customers) and your market segments. So often salespeople are selling to pretty much anyone, with no appreciation of who matters most, and why they really value your product.

Back in 2018, like most start-ups, Currencycloud had little to no categorisation into segments, it was a free for all, with sales doing deals left, right and centre. And we were growing, but struggling to properly scale.

What’s more, we weren’t really monetising the value we brought the customer in each sale and leaving huge amounts of money on the table:

  1. What’s the value we create?
  2. Where do we have real PMF?
  3. Where can we see large expansion revenue?
  4. Which are our best segments?

We were playing in over 30 identifiable segments if you use the Crossing the Chasm definition, which is that the accounts in the segment will self-reference. And you realise you have a growth opportunity when a salesperson is selling to a regulated FX broker one day, and to a digital bank the next, and because they use the same product, assuming the proposition, value and price should be the same.

Once we started to understand the segments and the value we quickly identified the opportunity to charge SaaS fees for the use of our platform (to complement the transaction fees), which allowed us to 3X the contract value. In the segments where we had strong PMF, the clients appreciated the value of the platform and were more than willing to pay. In fact, to help us put a price to it, we started to better extol the virtues of the platform which hitherto they might have either taken for granted or only discovered post-implementation was valuable to them. 

We didn't transition to be truly segment-led overnight because we didn’t have the critical mass of roles to support that level of assignment, and also it seemed just too bold a step. Instead, using the analogy from Crossing the Chasm, where segments are bowling pins,  we created three “bowling alleys” or groups of adjacent pins; “fintech”, “banking” and “FX broking”. The teams worked hard to understand the segments within their alley,  focusing methodically on the most valuable segments and “knocking over the pins” with wins. 

Bowtie thinking

We were aggressively focused on customer acquisition like any startup  - it was the classic more transactional FX broker mentality - but we didn’t do so well with those customers on the back end. I’m a big fan of Winning By Design. The work our team did to introduce the concept of the bowtie model was a turning point for me. It’s a powerful mental model to help us think as much - if not more - about the post-sales funnel as the pre-sales funnel.

I had inherited a devoted team of what we called Relationship Managers, which together with a talented but exhausted Customer Support team, struggled to keep up with the demands of an ever-growing customer base.

We had no structured approach for onboarding and adoption and therefore little hope of maximising flow once we had a client. We were winning ideal customers but not being especially proactive after the first purchase to drive incremental value and revenue expansion. I don’t know what our Net Dollar Retention was, because we didn’t measure it, but it certainly wasn’t world-class.

Customer Success as a function simply did not exist. But inspired by an event hosted by Notion, listening to a Gainsight presentation, two members of my team wanted to take on the challenge of a total transformation of the right-hand side of the bowtie.

They built a super effective new Customer Operations team (the reactive side of support), while investing in training to evolve the old Customer Support team into an impressive proactive Customer Success team, and the final step; resetting expectations of the old RM team to become proper commercial Account Management. 

Winning By Design’s Sales-as-a-Science really spoke to me, perhaps it’s the physicist in me, resorting to first principles and questioning everything.  It gave us the ability to think of sales and success as a repeatable process, with the ability to introduce marginal gains along the way.

Introducing Pods

So mid-2020, 24 months into my tenure at Currencycloud, we had clearly defined roles across the customer life cycle. We were ready for the move from alleys (which was a pragmatic fudge) to really getting deep into the customer segments. 

To improve the top of the funnel, we invested in SDRs and more campaign marketing managers, which delivered the critical mass for us to assign them to their own segments (or groups of segments if they were small or undeveloped) within the alleys.

But we worried that individuals were too often working in isolation, despite our best efforts to devise optimal hand-offs between the roles and the games in kick-offs to encourage teamwork. We felt sure that we could do much better in acquiring and developing the best customers in an increasingly repeatable manner.

The catalyst for change came from two sources:

  1. The individuals in the Banking alley (our smallest team) on the right-hand side of the bowtie (implementation, account management and customer success team members) started to naturally bond and collaborate around their segments, ignoring our relay-like hand-off advice and instead instinctively running with a more of a tag team approach to drive customers’ success.
  2. Our executive team had workshops with Patrick Lencioni’s consulting business, The Table Group, which totally inspired many of the GTM leadership with ideas on leading organisationally healthy businesses.

A few months into the pandemic, with teams at home where we couldn’t rely on organic office-based teamwork, made more threatening with our intention to almost double the size of the GTM organisation, we took a deep breath and embarked on the move to establish “Pods”. 

Pods have a minimum of seven members serving all the roles across the bowtie (but we added product representation too, to listen and act upon PMF improvements), all focused on a single market segment or collection of 1-3 smaller adjacent ones. We ended up with ten Pods worldwide.

We had three different types of Pods driving different types of segments: 

  • The majority were focused on segments we called Optimise Segments, which as the name suggests were focused where we had good PMF and their task was to obsess over the marginal gains to drive incremental revenue growth and the CAC reductions that come from customer advocacy. These were our growth engines.
  • Then we had Pods focus on Development Segments, which were emerging segments with good but not predictable wins, and their mandate was to get them to a point where they could move to Optimise. To establish new seams of growth.
  • Lastly, we had Discovery Segments, to help us open new rich seams of growth, where the Pod focused on segments and accounts where we really weren’t sure that we had the necessary product capabilities and value. So their role was to qualify segments in or out, and if in, move them to Development. In these segments, we may be getting spotty inbound leads, but the conversion and churn were terrible. So the mandate to the Pod was simple: Figure it out. Real start-up stuff.

High performing teams

So we had groups of people aligned around core segments. All the focus and alignment we needed but they weren’t teams.

Our executive team had gone through The Table Group training and it really worked, Like many of us, I had already read Patrick’s “The Five Dysfunctions of a Team” and it struck us that the model we applied to the exec team could also work with the Pods - building a foundation of vulnerable trust, mining for dissent, having passionate unfiltered debates, establishing peer-to-peer accountability, to deliver better results -  it was instrumental in driving the behaviours we needed to make the Pods autonomous and accountable. 

We rolled out The Table Group methodology, remotely, in intensive sessions early in the pandemic. For many, it was their first experience with Currencycloud, and it was, and still is, invaluable. My favourite quote after onboarding into the new ways of working was from a new Customer Success Manager who said: “it was one thing to be held to account by my manager, but now I’m being held to account by my peers and I love it!”

Building on the values

And so we come to values. I’m sure Pods could not have worked without our values being the foundation stone to build upon.

Currencycloud’s values, which I always felt were naturally established by one of our founders, Steve Lemon, and were later codified, were simple and powerful: Be Human; Better Together; and Own It.  Steve really embodied these values.

In conjunction with The Table Group, we started to build on the criticality of these values in the Pods and the importance of people living them and taking ownership of them.

  • Be Human? Much more than being “nice”. It’s about establishing psychological safety.
  • Better Together? Ideal for a Pod team, but has a surprising edge to get the best outcomes
  • Own it? We gave the Pod accountability. If there are problems you fix them.

The interesting thing about the Pod structure is that it mirrors the early startup stages and that really appealed to us.

Driving Excellence

With the bowtie model, a clearly defined customer lifecycle, and a Pod structure we were in a great position. But if we want to answer the question of whether we can grow faster then we need data across the life cycle, understanding the maths that underpin growth - basically conversions and speed. That’s where our Revenue Execution function comes in.

The purpose is to drive excellence across our GTM effort to very much turn it into more of a predictable well oiled machine. The Revenue Execution and Sales Ops team has the data to understand what is working and what is not, which allows the Pods to focus on marginal gains to optimise their strategies and push growth to the limit. While the team's leader brings the persistence and support of a sports coach to ensure that no stone is left unturned to improve.

The essence of the Revenue Execution function is to help all our teams find repeatability, optimise and drive marginal gains.

So What?

The culmination of our focus on value, focus on the customer, building Pod teams around our segments, and wrapping it all in a culture of high performance led to sustainably driving 60% growth each year, with world-class Net Dollar Retention of over 140%, while taking our NPS scores from high teens to over 60 (while similarly ramping an employee NPS to over 80 for the GTM team).

Since 2019 we’d established a partnership with Visa, which at the end of 2021 converted into an acquisition for $1b.

Mistakes to avoid, and how to avoid them

The most important mistake that is often overlooked, is not getting help to avoid mistakes!

Find mentors and guides. Your VC may run a programme to support their portfolio with best practice insights  (Notion certainly does this brilliantly) or even be able to introduce you to some grey hairs that have been there before. There is an investment in time, OpEx and perhaps equity to get help - but imagine the lost revenue, missed expectations and stress of the alternative - as you work it all out for yourself…

The most common mistakes I’ve seen happen:

  • Thinking that hiring the superstar sales leader from a well-established company will sort your growth problems out. It won’t, unless they were part of building that business, they have benefitted from simply executing on the PMF and GTMF work of their predecessors, and will rarely know how to achieve scale.
  • Generally thinking that sales can do the PMF work - different skills, they can test a thesis, but lack the product rigour and patience to discern the real customer pain.
  • Expecting scale from a market segment before you have repeatability 
  • Wholesale copying an approach from elsewhere and expecting to get the same result. Your situation will almost certainly be importantly different.
  • Too often I see founders assume that revenue is only about sales executing properly. No, sales is where the effectiveness of the whole business to be customer success centric is tested every day, including of course sales. Success is a whole company thing - everyone playing their part.
  • Working inside-out, versus outside-in. It’s a big mistake to be overly focused on what we want, versus being focused on what the customer wants. It’s a culture thing - sustainable world-class growth and revenue happen because the whole org actually cares about the success of the customers we target. 
  • Asking the sales team to make the choice of what they stop doing to focus - they won’t. Focus is hard, leaders make this call for them
  • Assuming customers won’t pay for the value you’re bringing - instead have real depth in your customer understanding and confidence in the value exchange.
  • Not investing in customer success is a big one - it’s all about adoption and advocacy in the SaaS game.
  • Assuming the culture that made your startup successful, will scale. It won’t unless you’re purposeful about what makes your culture special, and then investing to perpetuate it as you add staff.

Have fun…

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