April 10, 2025

Revolutionizing B2B Marketing: Unleashing the Power of SMS and AI

A strong RevOps strategy aligned across marketing, sales, and customer success is essential for startups to scale efficiently, avoid silos, and build a sustainable revenue engine from day one.

In today’s competitive business landscape, startups face numerous challenges when structuring their organizations for growth. One of the most critical yet often overlooked components is establishing an effective revenue operations (RevOps) strategy from the beginning.

Recently, I had the opportunity to speak with Chelsey Reynolds, founder of Asterios and a seasoned revenue operations leader with over a decade of experience. Chelsey specializes in helping companies set up their revenue organizations—encompassing marketing, sales, and customer success—to prepare businesses for scaling effectively.

The Foundation: What Is Revenue Operations?

Revenue operations, or RevOps, is a relatively new function that has gained tremendous traction in recent years. By 2026, an estimated 75% of companies will have some form of RevOps strategy in place. But what exactly is it?

At its core, RevOps creates a unified approach to driving revenue by aligning marketing, sales, and customer success under one umbrella. Instead of operating in silos with separate goals and metrics, these departments work together toward common objectives with shared accountability.

“Marketing, sales, and customer success should all be on one revenue team,” explains Chelsey. “When you’re very young as a company, your RevOps strategy can be simple, but if it’s aligned, you’ll see a flywheel effect happen.”

This flywheel concept contrasts with the traditional sales funnel that ends once a customer purchases. In the flywheel model, happy customers become advocates who generate referrals and expanded business—creating sustainable growth.

Starting Right: The Startup Challenge

For early-stage startups, the organizational structure often develops organically and reactively. As Chelsey points out, “Traditionally, you’d find the CEO is a little strapped, so they’ll add on this role over here or that role over there as they need help.”

This approach creates disconnected departments working in their own tools with their own processes—even in companies with just a handful of employees. The result? Toxic finger-pointing between teams:

“The leads suck.”
“Why did sales sell it this way?”
“Why isn’t sales following up on the leads we gave them?”

This internal friction inevitably affects customer experience. “We’re kidding ourselves if we think customers can’t tell that nobody’s having fun at work,” Chelsey notes.

The CRO Question: Who Should Lead Revenue?

One of the first critical decisions for startups involves leadership structure. While the traditional hierarchy might place individual leaders over marketing and sales separately, Chelsey recommends a different approach: bringing in a Chief Revenue Officer (CRO) early.

“The CRO title wasn’t huge a few years ago, and now it’s one of the fastest-growing titles,” she explains. This person oversees the entire revenue organization and ensures alignment across marketing, sales, and customer success functions.

For very early-stage companies, the founder or CEO might initially handle the revenue leadership role, depending on their skillset. The key is auditing all the tasks that need to be accomplished:

List all revenue-related activities the company needs to perform
Determine who’s currently doing each task
Rate (on a scale of 1-5) how much each person enjoys and excels at each task
Identify gaps where fractional help or new hires are needed

This analysis helps founders recognize when it’s time to bring in specialized talent—whether full-time or fractional—to drive revenue strategy.

Common Startup Hiring Mistakes

According to Chelsey, early-stage founders typically make two critical mistakes when building their revenue teams:

1. Hiring the Wrong Profile

Many startups face a dilemma: hire the industry “hotshot” with name recognition or the scrappy executor who can roll up their sleeves? For early-stage companies, Chelsey strongly recommends the latter.

“They’ll hire someone who’s a hotshot but doesn’t know how to get down in the nitty-gritty and has been a little too high up, hasn’t been doing the stuff, and has had an army of people doing this for the last 5-10 years,” she explains.

While these individuals bring impressive resumes, they often lack the hands-on skills needed in resource-constrained environments. Early-stage startups need leaders willing to execute, not just direct.

2. Settling for Mediocrity

Equally problematic is the tendency to hire friends or keep underperforming team members due to personal relationships.

“You settle for the wrong people… having friends come in and then just keeping mediocre people around,” Chelsey notes. “You’ve got to be ruthless and very careful with your budget of who you have on your team because good people will leave.”

The Micromanagement Trap

Beyond hiring, another significant pitfall for founders is becoming a bottleneck through micromanagement.

“If I’ve got to tell you to do something, then I’m like, I don’t like this. I’ve already told you once,” shares Chelsey. “As a leader, I should just be able to say, ‘Hey, I need a go-to-market strategy that’s going to help me achieve X, Y, Z, and I need that in the next month.’ Boom. Done.”

Micromanagement not only frustrates talented employees but dramatically reduces overall productivity. Instead of executing, team members spend excessive time creating status reports and attending check-in meetings.

Signs you might be micromanaging include:

Doubting your team members are working hard enough
Feeling that if something needs to be done right, you must do it yourself
Requiring excessive documentation of daily activities
Constantly checking in on progress

If these patterns sound familiar, Chelsey recommends working with a coach to develop more effective leadership approaches.

Building a Sustainable Revenue Strategy

Creating a sustainable revenue strategy requires discipline and focus. Chelsey recommends being “ruthless with the goals, the hiring, and saying no.”

Many founders get distracted by “shiny object syndrome”—constantly pivoting to new opportunities or product features without fully executing on core initiatives. This problem often manifests when:

Board members suggest new directions
Customers request custom features
The founder spots a potentially larger market

The solution? Document priorities clearly and have team members who will push back and ask “why” when new initiatives threaten to derail focus.

“Have a conversation, but you have to push back. Don’t just say, ‘Okay, well, the CEO told me to do this. Now I’m going to go do it.’ Why? Be obnoxious. It’s actually going to save the company a ton of time and money,” Chelsey advises.

Tools and Metrics: Keep It Simple

Early-stage startups don’t need complex tech stacks. Chelsey recommends answering these basic questions first:

Where did my customers come from, and how much did it cost to acquire them?
How much are my customers paying, and how long are they staying?
Are my customers happy, and are they seeing value in what we’re selling?

For tools, she suggests starting with spreadsheets for very early companies, then moving to platforms like HubSpot, which offers marketing, sales, and support functionality in an affordable, easy-to-learn package.

Most importantly, avoid tool proliferation. Chelsey shares an example of a 20-person company using Outlook, Slack, Teams, OneDrive, Notion, Fireflies, and HubSpot—creating confusion about where information lived.

“Start with one [platform] and make that the central source for everything that you do. So everybody’s required to keep putting it in there,” advises Chelsey.

The Personal Branding Factor

As startups grow, personal branding becomes increasingly important for founders and revenue leaders. While not everyone needs to be a social media influencer, authenticity matters tremendously.

“As long as you’re authentic and you deliver what you say you’re delivering, I think those are the two most important things as a leader,” Chelsey explains.

This applies particularly to product claims. Overpromising capabilities that don’t exist yet has sunk many startups. As Chelsey emphasizes: “If you can’t do it, don’t say you can. Don’t go out there and watch a solution at a show that you plan on having [but don’t yet]. Make sure it actually works.”

Final Advice for Scaling Startups

Chelsey offers two critical pieces of advice for founders looking to scale:

Decide what type of company you want to build. Is this a lifestyle business where you’ll grow slowly but sustainably? Or are you aiming to “go big or go home” with rapid scaling? Both are valid, but they require different approaches.
Hire great people and get out of their way. “Get good people around you and trust them to do their jobs. Give them the tools they need, and then get out of the way.”

For those looking to improve their leadership approach, Chelsey recommends the book “Fierce Conversations” to help founders build a culture where challenging questions and accountability thrive.

Her final piece of wisdom? “Get curious before you get furious.” By asking questions first and assuming the best in your people, you’ll build a revenue organization capable of sustainable growth.

Revenue operations isn’t just another business buzzword—it’s a fundamental shift in how successful companies align their customer-facing teams. For startups looking to scale effectively, establishing a unified revenue strategy from the beginning creates the foundation for sustainable growth and avoids the painful silos that plague so many organizations.

By focusing on alignment, hiring the right profiles, avoiding micromanagement, and maintaining disciplined focus, startups can build revenue engines that drive long-term success.