CRO Confidential: Why Your Startup Needs A Rev Ops Leader With Cherishma Shah, Senior VP of GTM at Guild Education

"A good range for your first rev ops hire might be between 2-8 sales reps"

Not every leader is created equally. A bad experience with a revenue operations leader might taint your view of the position at all future companies, but that would be a mistake, as CRO Confidential podcast host Sam Blond learned first-hand. 

In this week’s CRO Confidential episode, Blond talks to one of the best revenue operations leaders on the planet, Cherishma Shah, where she shares insights into the Rev Ops role, why your startup might need one, and how to maximize impact with this powerhouse position. 

Shah is the Senior Vice President of Go-To-Market Strategy, Operations, and Enablement at Guild Education and formerly held the same role at Brex, working alongside Blond. 

And listen to the pod version here:

Revenue Operations Is Much More Than Sales

Revenue ops aren’t just GTM, GTM strategy and ops, sales or marketing ops, but you’ll see these titles and roles in various companies. 

Rev ops go across the entire sales cycle, starting at sales and moving through customer success, implementation, and every other step along the customer journey. 

Shah’s definition of revenue operations includes things like: 

• Laying out the operational foundations for how an organization thinks about these functions and how they grow.
  

  
  Examples: Consistency of methodology or how a company thinks about territories and incentive plans.  

• Considering aspects of sales and GTM strategies. For example, how do you think about ICP, and what markets should you go after?  

• Enablement. And not just the content of enablement but the process of it.

As it applies to any GTM organization, the function of operations incorporates systems, process, strategy that combines data analysis and driving strategy trends, and enablement. 

Sometimes this function begins dedicated to a specific department like sales and marketing or customer success but eventually expands to include revenue or GTM operations, tying all of these functions together. 

The Right Time To Hire A Dedicated Rev Ops Person

What you typically see at a company is someone saying, “hey, I have more than two sellers.” They start to consider defining their sales methodology and standard processes and thinking about incentive plans. They seek out someone for campaign management and leveraging the right tools for marketing. 

When we see this hire, it’s usually viewed as a tactical person to run analysis, do assistant work, or run campaign management. 

Shah encourages companies to think beyond meeting these immediate needs and, instead, bring on a dedicated rev ops person or team sooner rather than later. 

The “right time” will differ for every organization. 

A good range for this hire might be between 2-8 sales reps. If you’re growing quickly and making a lot of sales hires, you might invest earlier. If you’re growing slowly, you’ll probably need less support on the strategy and operations side of things early on. 

Some questions you can ask yourself when determining the right time to make a rev ops hire are: 

1. What is the right level of growth for my company? 

2. How do I think about scale? 

3. What does a productive seller mean? 

When hiring for rev ops, you’re hiring a partner in crime to the sales leader. You want to bring in someone who asks those questions, has a slightly different skill set than the people you already have, and thoughtfully pushes against what you want. 

Hire A Leader

When making this hire, you’ll choose a specific skillset based on your company’s needs. It might be a systems person or someone deep in data analytics who can quickly translate different data points. Others might start with enablement because it’s their biggest issue. 

Shah argues that people should start with a leader first, if possible. These leaders act as partners and build out a strong team. They set foundations, hire the right people, and shape what success looks like for an organization. 

To determine what kind of profile you should hire for, figure out the answer to these two questions: 

1. What are the responsibilities you want this person to own?  

2. Do you want just one contributor for now, and as the business grows, this person pairs with a manager to build out the team, or do you want to start with a leader? 

Mistakes To Avoid When Hiring For Rev Ops

The biggest mistake many companies make is waiting too long to hire this person. 

The potential downfall of waiting too long is that when certain things get embedded in the organization, changing them becomes more challenging and resource intensive. 

So companies will want to constantly think about this hire, even if it isn’t the first one. Determine if you want to invest in a team leader who helps you scale first or hire for specific areas you want support in.

Another common pitfall for hiring someone is looking for an exact industry fit — someone who’s worked in this industry for this type of product serving this type of customer base. 

When considering a skillset, Shah recommends hiring a generalist, not a specialist. You want someone who can dip their toes into many areas and communicate with a variety of people across the sales cycle. 

Generalists are strongest at connecting the dots rather than only looking at their pieces of the puzzle. 

Instead, solve for core capabilities rather than exact fit. 

Where Rev Ops Leaders Can Make The Biggest Impact

If you join a company as the first revenue operations leader, you can make the biggest splash in a few buckets based on your industry or company’s problems. 

1. You can build a strong analytical foundation.
   
   Lay the groundwork for metrics that tell you what success looks like. Determine what good looks like for both input and output. What does good look like as a productive seller? What should velocity look like?
   
   These metrics and insights evolve into good decision-making down the road.  

2. You can create foundational processes.
   
   Develop a sales methodology. Ask yourself how you work with your partner teams and the roles and responsibilities between sales and solutions architects, or sales and post-sales transitions.  

3. Test processes and put them in systems.
   
   You get to define a process and do a few revisions outside the system before putting it into a tool. Take your time here. It’s ok to work out of Google Sheets for now before deciding if the new way sits. If it doesn’t, you’re free to scrap it.  

4. Determine early markers on GTM strategy.
   
   What segments should be prioritized? What should the GTM approach be? How do you hire against these markers? Determining early markers will give you a path to follow while making decisions for the organization. 

Measuring The Success Of A Revenue Operations Hire

Measuring the impact or success of a rev ops team might seem subjective, but you can create clear, objective data points. 

How do you do this? 

By determining what success looks like. It’s difficult to measure if someone is a good influencer. The point of an influencer is to feel like you came to a decision together. 

So for this team, clear objectives are essential. Some potential metrics might be: 

• A forecasting process by the end of the quarter

• A sales methodology definition by the end of the quarter

At Brex, Blond talks about how there was a lot of variance in data around deal sizes. Everyone had free reign and loose guidance on who to go after, leading to this deal size discrepancy. 

Shah made a dedicated hire at the time to own the issue. They put in place a sophisticated lead scoring and activity predicting and recommending system where everyone could see an estimate of what kind of revenue a company would generate. 

By automating the subjectivity of this problem, the sellers were more effective, leading to a 3x increase in the average opportunity size. 

Talk about a clear objective with measurable results. 

Key Takeaways

When you hire a dedicated rev ops leader, you want them to act as a business partner to whoever they’re working with. As far as structuring, they need to be peers to the people they’re working alongside to give them a certain level of freedom to push back and challenge those peers. 

Some of the key takeaways for hiring a rev ops leader for your organization include: 

• Your rev ops leader must be cross-functional to support the sales cycle across the entire customer journey.  

• Be intentional about when you hire for this role and who you hire. If you’re growing rapidly, find someone early on, and determine if you want a leader and business partner to grow your company or someone to solve a specific problem.  

• Hire for core capabilities vs. exact industry fit. Generalists tend to be stronger at connecting the dots throughout the sales cycle.  

• Create clear, measurable objectives and use those metrics to determine the success and impact of the rev ops role.