From VP of Sales to Chief Revenue Officer (CRO).
Priorities shift. Responsibilities evolve. All while your company continues to grow and excel.
Not an easy transition.
Yet we see it happening in revenue-centric organizations across the world. Your decision-making must adapt to shifting dynamics and the broader scope of responsibilities if you hope to find continued success.
Robby Allen is the CRO at AgentSync. He believes that “the most important thing I can do as a leader is hire, develop, and enable great people. I've learned this lesson at every stage of my career.”
In February of 2022, Robby made the leap from VP of Sales to CRO.
In this article, Robby shares the ins and outs of that transition and provides some key tips to (1) help make the move as seamless as possible and (2) how to work best at different stages of business growth.
But first, let’s discuss his favorite topic: Revenue.
Running revenue at various stages of company growth
The skill set required to run revenue at an early-stage company versus a growth-stage company is “fundamentally different,” says Robby.
Very few people have successfully made the leap from a zero to $10M, to a $50 to $100M company.
Based on what Robby has seen (and done), here are a few suggestions at each stage:
Zero to $10M in sales
In the early days of an organization, the first iteration of sales is typically led by the founder(s). That responsibility then goes to the Head of Sales, who is also often in charge of recruiting and RevOps (and sometimes marketing).
As Head of Sales, you are in all the deals — selling. Your job is to understand the best formula for success so you can replicate it for future salespeople. Can you move from 1 sales rep to 2 to 4 to 8 (and so on) while scaling revenue?
Many companies don’t make it out of the “zero to one” sales phase. Why? Finding repeatability is really difficult. It takes someone who is scrappy, a person who is willing to get into the weeds and run deals themselves.
But it also requires a person with the foresight to understand they must work themselves out of their job.
$10M to $25M in sales
If you can successfully move past that first stage, you are now in the $10-$25M zone. This is where forecasting and “being right” about quarters and months is essential. Missing your number can impact fundraising, a Board of Directors, and your team.
It’s during this stage when focus shifts from a “repeatable process” to “identifying the customer persona who has the highest propensity to buy”. It’s when sales process rigor, consistency, and forecasting become critical.
In the $10M-$25M stage, you are becoming very comfortable in your sales process. When forecasting deals, you know certain things are true, depending on the stage where these opportunities live.
Finally, this is when you evaluate the diversity of your revenue streams — moving from one product or service to many. You may also consider selling more usage or consumption of the existing product. You must think about the world a couple of quarters into the future, and your forecasting accuracy has to be spot on.
$25M+ in sales
This is often when a company is (ideally) starting to see double-digit revenue growth.
This is where scale matters — the ability to add capacity into your revenue model, often by increasing sales headcount and quota. In this stage, we often see account managers selling into your existing book.
Inside sales. Outside sales. SDRs.
Enablement. Onboarding. Scale demand gen.
You are now leading leaders, influencing more — especially the long-term product roadmap.
You no longer have the time to “pull levers” to get one or two extra deals over the line. Your focus is now on process and governance. This governance, in turn, helps drive that rigor and accountability around the forecast.
As a CRO, the sales team is not your team; your executive peers are now your team.
Let’s look at a few other differences when moving from sales leader to CRO.
From running an inside sales team to CRO at a growth-stage company
The biggest “scope change” during the transition from running a small inside sales team to becoming the CRO of a high-growth stage company: customer business expansion, cross-selling, upselling, retention, and so on — these are now added to your priority list.
The key to a CRO’s success, according to Robby, is clearing hurdles and giving VPs space to run.
Robby also thinks a lot about “revenue diversification.” Many revenue leaders were spoiled during the business-friendly years (2020 to 2022) — zero interest rate phenomenon, lots of venture capital fundraising, and sales reps making their number halfway through the year.
“It was a bit of a gold rush. And then ... we came back down to earth (in 2023)”
This “good times” period exposed the need for companies to be much more mindful of the quality of both revenue and customers.
You need to ensure your customers who are exposed to these macroeconomic conditions can “withstand the headwinds.” Do the products you are building fit the ideal customer profile you're selling to? Are these companies that have the durability to be a customer for life?
One way to do this is to give CSMs quotas around retention — the same retention quota AEs used to own for renewals on their own. This helps not only with alignment, but also getting the entire organization to understand what quality customer revenue looks like.
But the other big change when moving into the CRO role is influence — influence to impact real organizational change.
How to influence change as a CRO
Influencing change within your organization is about “bringing people along for the journey” and ensuring you understand the different perspectives of executives on the team. You need to “get their fingerprints on the change or the work to be done,” says Robby. “You must ensure you're enlisting buy-in and feedback ahead of time.”
Robby also stresses the importance of not making assumptions and always being curious.
Mistakes at this stage have far greater consequences due to your reach and impact — the ability to impact everybody in the organization.
Here is the thing: If you don’t have a solid cross-functional foundation and you don’t get relevant executive team members to buy into the vision, your change will never work.
Leave no revenue behind
The job of CRO and the skill it demands fundamentally differ depending on the company stage — early vs. growth.
As a CRO, you must adapt quickly to market conditions and be able to influence organizational change. The role requires a blend of sales expertise, strategic thinking, and leadership skills — challenging and dynamic.
And at the end of the day, you are judged by one thing: Your ability to drive long-term, sustainable revenue.
You must run revenue like a process. You must create a consistent and repeatable cadence of revenue moments.