How Flow State helped Charlie boost their close rate by 9%

Results at glance:


Close rate
increased from
29% to 38%

Target attainment increased from
116% to 131%

Average deal size
increased by
over 12%

Charlie has built its business on one core belief: Companies that focus on their people will always outperform those that don’t. The easy-to-use platform helps small businesses automate HR tasks, manage processes and keep all their team data in one place, enabling them to build a great workplace culture.

Timi Olotu is the Director of Revenue at Charlie, responsible for the sales and marketing organisations as well as the company’s overall commercial strategy and performance. He joined Charlie in 2021 as part of a long-term strategy to become more commercially focused and effective.

“Our ultimate goals are very macro,” he explains, “but to achieve those I need to make sure a lot of micro things are working well.”

At a high level, that means ensuring the business acquires customers quicker and that its revenue growth rate is high enough. It also includes an element of change management in terms of the culture of the company, teams, people and performance standards.

On a day-to-day basis, this involves understanding the individual components in sales, marketing and any related functions that need to be in tip-top shape for Charlie to hit its target annual growth rate. Timi then works with the people who head those specialist areas to ensure that’s happening.

“I’m a big believer in thinking of myself as an investigator rather than a genius. I don’t come into a job thinking that I have all the answers, that I know everything there is to know about sales and marketing.”

For his role at Charlie, Timi started by appraising the situation as thoroughly as possible, auditing areas like marketing operations, sales operations, strategy and tactics. This revealed a limited sales operation.

“It was essentially just people talking to entirely inbound leads in whatever way they felt was best. There was no sales process, no sales strategy, no sales structure, no pipeline management process, no forecasting process — it was just very underdeveloped and, as a result, it wasn’t performing at the level that we needed it to.”

Perhaps more importantly, the lack of any defined process or methodology meant it was impossible to see where deals were falling through the cracks.

In all, Timi identified three main layers of underdevelopment:

“I knew I couldn’t tackle all three layers myself, so I decided I would tackle the operations and outsource the sales methodology and skills training to Flow State.

FHaving previously worked with Raff and Aaron at a different company, Timi had already seen some of their sales training sessions and how they operate. He’d also had the opportunity to watch a lot of their online content, which resonated with him.
“When it comes to sales training and strategy, I rarely see content of that quality. We all know what sales and marketing content is usually like; usually people trying to sell pipe dreams and get-rich-quick schemes — very shallow, superficial, simplistic advice. But with Flow State, I could see that their videos were comprehensive and outcome-focused.”

While Timi had already identified the main areas that needed overhauling, one of Raff and Aaron’s first objectives was to diagnose the sales team’s performance and determine the specific competencies to include in the training. This involved a few sessions going through the possible curriculum before talking with Timi and the sales team about where the biggest gaps were and which areas to focus on.

After this initial analysis, Flow State implemented a programme covering three main facets:

This advisory role was particularly valuable to Timi, allowing him to bounce ideas off the Flow State team and be confident in the work he was doing on sales operations. “I would consult with them and say “Here’s what I’ve put together. What do you think? Can you audit it? Can you help me streamline it?"

This guidance extended to other aspects of the overall operations, including aligning sales and marketing with customer success as well as optimising recruitment, providing Timi with feedback on his approach and advising on the type of candidates to look for.

By putting clearly defined processes and methodologies in place and training the team against them, Timi saw a significant positive impact on the team’s sales performance. Close rate increased by 9% and target attainment both increased by 15% after the engagement.

There was also an increase in average deal size came, which came as a surprise to Timi; with no suite of products, there isn’t much opportunity for reps to upsell or cross-sell. Charlie’s scalable pricing is based on company size, so bigger companies pay more, but that also usually means more complex deals and more sophisticated requirements — something that had previously been a challenge for the sales team.

However, as a consequence of Flow State’s training and coaching programme, the sales team recognised the importance of the discovery phase. While reps would previously spend five minutes (at most) on basic discovery, after the training they were doing anywhere from 30 minutes to an hour of high-quality discovery work.

This gave the reps a far deeper knowledge of the prospect.

They were able to pick up on the key components of a healthy deal such as the prospect company’s compelling event, champions, decision-makers, timelines and budgets. By collating this information in a better and more structured way, the sales reps were in a much stronger position to have persuasive conversations with these bigger clients. As a result, the average deal size increased by 12.13%

Timi’s favourite part of the training programme was Flow State’s willingness to take the sales team to an uncomfortable place, balancing empathy with forthright honesty. “Growth is often uncomfortable,” explains Timi. “So anyone who’s going to truly help you grow has to be willing to take you somewhere uncomfortable.”

To achieve this, Raff and Aaron worked closely with the team, embedding themselves in the company and building relationships with the reps. This allowed them to challenge the sales team without it coming across as an attack or in any way negative.

This resulted in cycles, where Aaron and Raff would work with the team to impart new knowledge, new expectations and new standards that they weren’t familiar with or comfortable with. This invariably led to the team being able to improve and level up their skills. In turn, they would feel more positive about themselves and their work, which led to better performance.

“One of our salespeople who was going through the training took a sales call at home, where her roommate overheard the whole thing. After she hung up, her roommate (completely unprompted) said to her: “Wow, you’ve gotten way better. What’s going on? What have you changed?” This roommate had no idea that this training was taking place, but intuitively felt that the sales call was way better.”

Since Timi joined Charlie, the company’s fundamental strategy has been to focus on the HR management software market and to improve its ability to attract and acquire new software customers.

Thanks to Timi and his work with Flow State, they’ve been able to solve a huge part of that equation. Even through the recession, they’ve managed to dramatically increase the demand for the software. Going forward, Timi wants to further improve their ability to close that increased demand.

Meanwhile, Timi wholeheartedly recommends Flow State to other SaaS businesses looking to improve their sales process. “There are many facets to the work they do, but the net effect is that each minute of your salesperson’s time generates a higher amount of revenue. They’re smarter about the way they think, they’re more organised, they’re more structured, they’re more strategic, they ask better questions, they make better decisions.

“All of that means that at the minute level, as they’re going through the day, they’re making more and more profitable decisions about where and how to invest their time. And Aaron and Raff give them all the skills they need to do that.”

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