Salesloft’s Katie Rogers on scaling customer success to support 2000% growth

8 min readSep 29, 2016

Salesloft has seen explosive growth, expanding its user base by 2000% two years in a row. Katie Rogers, VP of Customer Success, shares her strategies for building a team strong enough to support such breakneck growth.

Katie Rogers, Salesloft’s very first Customer Success Manager and now VP of Customer Success, knows change is the only constant.

Having transitioned into SaaS from an international hospitality corporation, joining Salesloft as the #7 employee meant embracing change from day one — and every day since.

“Coming to Salesloft could’ve definitely overwhelmed me if I’d let it,” she said. “I was taking off the suit, putting on the t-shirt and embracing so many new things — new vocabulary, new speed of working, new ways of thinking about growth.”

Since that transition, she’s helped develop a company that’s expanded its user base by 2000% two years in a row, and built out the customer success team responsible for supporting that breakneck growth.

Here, Katie shares the strategies behind the rapid expansion of her team, and lessons learned in the journey from SaaS novice to VP on a $10M ARR rocket ship.

In a hurry? Your key takeaways:

  1. In the earliest days, there will be an endless list of tasks fighting for your attention. To forge ahead, focus on one long-term priority at a time.
  2. It’s tempting to hire someone as fast as possible to share the workload and create more time for strategic efforts. Resist this urge until you’ve optimized your own workflow and automated as much as possible.
  3. As a leader, acknowledging the gaps in your own skill set is crucial to rapid growth. Look at which goals you’re struggling to hit, and hire for the skills needed to reach those goals.
  4. Eventually, you’ll no longer be able to touch everyone on the team. To keep people motivated long-term, develop a culture others can own, even when you’re not there to enforce it.
  5. At a startup, giving employees a concrete plan for career growth is challenging. To build motivation, put employees in charge of deciding which skills they want to develop. Once a related position does become available, they’ll be ready for the new challenge.

The early days

Find ONE priority in the chaos

From day one, Katie had an entire stack of plates to keep spinning. There were the 72 existing accounts and several hundred users to manage, waves of new accounts coming in every day, and a complete lack of infrastructure to support everyone.

So she had two options: bury herself in the daily responsibilities of customer success, or figure out what long-term effort could decrease her workload — and hone in on that.

“I had to zero in on one need,” she said, “and that was figuring out: what were the main questions coming back from customers? What answers did I keep having to give people over and over?”

Carving out time to identify FAQs enabled Katie to create Salesloft’s first knowledge base. It was a massive project that “took a lot of long hours,” but once complete, she saw a 20% reduction in emails back and forth with users.

“By choosing that one priority — instead of trying to tackle several initiatives at once — I was able to automate a big chunk of my low-level work much faster,” she said, “which then freed me up to be even more strategic.”

Technology first, talent second

Like almost every early-stage employee, Katie was doing the work of at least two people (if not more). Even so, she knew that hiring wouldn’t be effective until she’d optimized the workflow alone.

“Hiring another client success manager would have sucked up my time with screening, interviewing, training,” she said, “which just wasn’t an option at that point. First, I had to look around and figure out what I could be doing to add more time back into my day.”

The answer? Tools before talent.

“I had to get faster at dispersing information to our customers, and cut out anything low-value,” she said, “So finding Calendly was huge. I’d been accidentally double-booking appointments and managing so much menial back-and-forth for months without even realizing it.”

Other necessities in her toolbox:

  • aText: write emails faster by creating keyboard shortcuts for long phrases you frequently type
  • screensharing / web conference platform customers can use from their browser, without having to download a desktop app
  • UserVoice: customer support / product feedback platform Katie used to track her speed of responses, customer satisfaction and the number of emails back and forth

“As a one-woman department, those were my game-changers,” she said. “Once I had my own workflow under control, I could start thinking about what kind of people we wanted to add to the team.”

From one-woman shop to lean team

Hire people you can learn from

Admitting where you’re falling short is one of the tougher sides of leadership — and it took Katie some time.

“I had to do everything in the beginning, but I also wanted to do everything,” she said.

“It took time to realize that we weren’t moving fast enough with me heading every project. We had to look at our metrics, and figure out which skills we were missing that would help us hit those metrics faster.”

For Salesloft, this meant bringing on customer success team members who’d developed their skills in highly nontraditional backgrounds — like Constance-Marie James, Salesloft’s Training Coordinator, who ran a tutoring business prior to her SaaS days.

“Constance is a training expert,” said Katie. “I learn from her every day, and she’s made such a huge impact here. That wouldn’t have been the case if I’d brought on another Katie Rogers. We needed someone who could really own customer training.”

Teach your team to motivate each other

The sharp ups and downs of client success can be draining, so celebrating the positives is crucial to morale. Katie’s a champion of in-the-moment praise, a practice taken from The One Minute Manager.

“When we’re all making client calls together, as soon as I hear something I like, I’ll send praise to that team member,” she said. “And whether it’s Slack, email, whatever, it’s important to share that praise with the entire team. When you do that, everyone knows how high the bar’s been set, and who set it. It’s a shared moment of happiness, and it’s also a chance for others to reflect on their own work.”

Incorporating praise into the everyday, rather than only in tough situations, has created a self-sustaining culture of positivity. Team members now boost each other up organically, whether or not Katie is in the room.

“I travel frequently now,” she said, “so if positive interactions only happen when I initiate them, one bad day while I’m gone could bring the entire team down. That’s why this active praise has been so important.

“Walking into the office after a trip and hearing praise fly back and forth between people, you just smile. That’s when you know the culture is real, and it’s something people want to stick around for.”

From lean team to well-oiled machine

Empower people to own their growth

Giving employees a concrete plan for career growth is challenging at a startup, where the role someone wants to advance to may not exist yet.

So to build loyalty and motivation, Katie puts team members in charge of their own career development — like her first hire, Aly Merritt, who transitioned to product management after about two years on the customer success team.

“Aly knew she wanted to work on product,” Katie said, “but when she came on board, we didn’t have a product team yet. So while she grew as a CSM, I had her go out and research the most important skills and responsibilities of a product manager. She built those skills on the side, so when leadership announced they were looking for product managers, I was able to raise my hand and vouch for Aly.”

Katie has helped her team members transition into roles across the company — marketing, sales, operations — and has come up with a few best practices:

  1. Encourage new hires to immerse themselves in their starting role for at least a year.
  2. Share with team members what growth options are available now, and what skills those options require. If those don’t appeal to a team member eager to move up, encourage them to be transparent about what they do want.
  3. Put the onus on them to figure out the responsibilities and skills of their desired role. Once they’ve identified those, help them create a development plan.
  4. Around the 9-month mark, connect people who want to transition with their peers who’ve already done so, to give them perspective on the culture and workload of different departments.
  5. Encourage people to seek out skill development, not higher titles. In a fast-changing company, being great at the work will be more rewarding (and make an employee more valuable) than taking a title that could become irrelevant.

Segment the team for invested employees and faster growth

In her short time in SaaS, Katie has already seen the customer success landscape begin to shift. Rather than an amorphous department made up of generalists (are they a support team? An account management team? A training team?), forward-thinking companies are seeking highly-skilled specialists to fill specific needs throughout the customer journey.

“Seeing CSM roles get specialized is exciting,” she said. “It’s a sign that companies are investing in customer success as a growth strategy. The thought is no longer just ‘we need a success person,’ but ‘we need this type of success person — analytical, technical, whatever it may be.’”

Katie’s tips are a good starting point for companies ready to leverage customer success as a part of the growth strategy — or companies already struggling to keep up with massive customer growth.

“Companies that give customer success the same authority as other departments will see more loyal team members and greater client LTV,” she said.

“We’re way past the days of customer services as a cost center. Two thousand percent growth doesn’t happen without a dedicated, forward-thinking team of CSMs.”

Claire Suellentrop is Calendly’s Director of Marketing.




When connecting is easy, your teams can get more done. Calendly is modern scheduling that makes “finding time” a breeze. Sign up for free at