Unlocking $15 Million ARR: 7 Essential Insights for Success

Every month, I settle into a small but helpful reflection that’s become a cornerstone of how I help advise my customers: My monthly preview. This process aims to help guide the support I’m lending to growing software and services companies.

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These questions ensure my advice is on point and support what’s truly important: making progress. ]

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The questions are:

• What got done?
• What worked?
• What didn’t work?
• How do we know it worked?

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It’s entirely based on personal experiences in a hands-on capacity over the years and what I’m observing dealing with an extensive portfolio of companies. I look to unpick what worked and, in today’s case, the enormous challenge of going from $2m ARR → $10 - 15m+ ARR.

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There are seven key learnings I’m about to share. I hope you adapt and create your interpretation of this insight to re-think your strategy.

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1. Partnerships are vital.

Partnerships often are poor relations regarding GTM (especially from a marketing lens) because so much of the focus goes on “Demand Generation or Creation”. Partnerships don’t ‘in theory’ deliver short-term revenue outcomes.

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This is a flawed mindset. Partnerships are one of the levers that will drive exponential growth in your revenue when it kicks in. It’s a route that can be genuinely scalable if you get it right. Hire the right person to lead it and ensure it’s given the time to kick in when it does; you’ll be grateful for the leverage it can deliver.

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2. Get an anchor customer.

Getting the right anchor customer can 10x your flywheel. Why? You can use the case study or story to sell to similar customers. If the customer is well known, it creates the FOMO in most cases to get deals done quicker. Be laser-focused on winning that anchor customer from a small list of targets. It will help drive your inbound simultaneously in specific verticals if people learn “what the #1 or #2 company is using as a tool.”

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Other benefits include selling through a story, use case and outcome of something tangible rather than selling your product. The anchor customer should help you retract your market to deep in that vertical, segment or market.

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3. Extra products.

Building new products or offerings on top of your core product is critical if scaling the revenue is above $10M ARR. From my personal experience, I have seen how the continuous layer of solving the following problem for the customer and making it easier to buy from one vendor is what your customer wants. But be careful not to offer products/services that do not solve the next challenge.

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An example of this would be if you have an awareness problem. You may find a product to attract 10,000 visitors to your site. Now, you should not upsell/cross-sell them a solution that gets them 30,000 visitors (that won’t be their problem). Their new issue will be converting your 10,000 visitors – that’s where you need to build the solution. Bonus tip: You must consider your GTM regarding “offer stacks”. This concept I came across a few years ago is connecting your different offers into pathways that connect (I am happy to show you this process if you want to reach out). Doing this enables you to scale revenue quickly and in a diversified manner.

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4. Outbound only bridges a gap

Post-investment, or if you are at $3 ARR - $7m ARR, you often believe the way to make the numbers is through Outbound marketing. Yes, the point can be valid. What I learned is I defaulted to this as a core strategy because there was no other way to visualise how on earth you’d hit the numbers (case-in-point learning being you need more levers, which I’m describing in this post). In short, outbound will only bridge a gap in the numbers. It will only partially get you to the number.

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I always see CMOs/CROs forecasting with this narrow view of the world. I don’t blame anyone; in many cases, it’s because, as said, the only viable approach is based on scaling revenue. The final (and essential insight) point is that outbound often creates a pipeline with “less intent” and “harder to close”. This happened to me several times. Outbound is a lever, but you must do it well (modern techniques that work, which I know and what I share with clients), and it must be part of the machine as a cog–not the entirety of the plan.

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5. Reputation builds brand

Operators need clarification about what building a brand stands for. When “brand” comes up in board meetings, discussions or budget cycles, there is always a frown of discontent like a dirty word. At the roots of it all, brands are about reputation. So don’t think of it as building your brand. Think of it more like “building your reputation”. The value of building a reputation is priceless.

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Reputation helps you attract more customers, close deals faster, charge premium prices, differentiate yourself from competitors and grow revenue faster. The focus of constantly looking to improve your reputation in the market is one part of the flywheel to drive results. The next time someone brings up a brand, flip the narrative and think about how you build your reputation in the market/ to your audience.

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6. A lot of marketing is wasted

One reason why marketing is wasted when in the process of this journey is because marketing is not fully defined within the company. It often gets treated as a demand gen function, a cost centre, a catch-all for everything, a sales support entity and many more. It means you build the wrong team, no team, and leaders are set up for failure. It means money is wasted.

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For example, you think marketing is performance marketing, so you hire people to do that function–they spend £300,000 on digital ads for 6-12 months only to realise you have the wrong ICP, the message of creativity. You built a new website for £50,000, which is already outdated after launch because it took nine months. I see this first-hand weekly, and as an operator, on reflection, I may have wasted some money. The wastage hampers growth. The first step to ensure marketing supports this journey is to have them focused on the right things in the correct order.

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In many cases, these are the foundations, customer challenge, differentiated POV, ICP, value proposition, market, message, and distribution. Correct these buckets, and then you’ll supercharge outcomes when you spend. I say the “marketing strategy is the business strategy.”

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7. Continuous optimisation of sales-people and process

Salespeople and processes are the last on my list. But one not to be overlooked. If you truly want to scale into the next phase revenue-wise, you must get this right. And no, this is not; go out and bulk hire sales-people and then send them into the market. This is not let's use MEDDICC, and everything will be OK. This is different from going and buying Salesforce or HubSpot.

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The whole idea of the sales function (and leader) has to be done thoughtfully. What are the baseline processes? How do you hire well, how do you onboard, how do you train, how do you scale sales enablement, how do you set the right metrics, what culture do you want to create, how to optimise for time spent <> revenue outcomes and what’s your continuous optimisation strategy.

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In my own experience, if this is executed well, and you have nailed the customer problem you solve, messaging to market, differentiated POV, know the segment/market you serve, position yourself effectively and nail the sales process/people side; the odds of success will be in your favour.

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To help you with the above. Review these ten items monthly /  quarterly to ensure the right processes are set in motion for success.

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Follow this framework to drive a well-structured and organised sales team. You need a plan for each of these buckets (resources below to help):

- Quotas

- Account Assignments

- Territory Plans

- Comp Plan & Fast Start SPIFF

- Sales Kickoff

- Pitch Deck & Certification

- Sales Process Implementation

- Win Stories / Customer stories

- Hiring Goals & Focus

- Team 1:1s / Team cadence

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In Conclusion

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This little monthly ritual has become invaluable in my journey as a CMO, advisor and GTM coach.

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It’s more than just reflection; it’s thinking deeper about what works as I learn.

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It’s making sure my advice is aligned with progress and actions.

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It also helps acknowledge the scaling challenges and that it’s hard sometimes not to do the obvious strategy (for example, 100% outbound play–it takes courage!).

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Give this process a try, and see if it works for you.

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Maybe you’ll have different learnings than mine above. In the end, I do know that those included in this post make a difference if you are getting out of that revenue range to $10m - $15m+; you need to think deeply about whether you are taking the right actions.

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Good luck out there.