“We’ve even closed enterprise deals off the back of coaching sessions because reps had sharper messaging, better qualification, and new strategies they wouldn’t have had otherwise."

"The conversations we’re having are better. The quality of pipeline has gone up. It’s a combination of their new willingness to get on the phone, to try new creative ways of working and new strategies… and I think that has been something so useful.”

JohnFounder & Ceo, Ask Bosco

PROJECT

Implemented ongoing 1:1 sales coaching across the team to replace ad-hoc, founder-led skills development with structured, personalised coaching.

WHAT WE DID

Integrated expert coaches into the sales team, giving each rep the freedom to choose a coach matched to their skills, role, and stage of development.

SOLUTION

Coaching sessions focused on the needs of each individual — without the cost or headcount of in-house enablement.

TIMELINE

Began with a short trial, rolled out to all reps after a few months, and is now ongoing as a core part of onboarding and ongoing team development.

Ask Bosco's Challenges

Limited founder bandwidth for consistent skills coaching and development.
Coaching time replaced by pipeline and deal discussions.
Risk of stagnation or attrition from lack of professional growth.
Existing training was generic and not tailored to individual needs.

Sales team at mixed experience levels requiring different types of support.
Desire to professionalise the sales function without increasing headcount.
Need for a scalable, consistent coaching model to support future hires.

🚨 Stretched Too Thin to Coach the Team Properly

As a commercial founder and lifelong sales professional, John Readman knew how important coaching was — but like many leaders, he was stuck in the weeds.

“A normal one-to-one with my team would just end up being pipeline or deals. Coaching on skills wasn’t really happening.”

“I used to do it all, and realistically, I wasn’t doing it well enough.”

“I knew I didn’t have the bandwidth to give the team what they needed — proper time, regular coaching, individual focus.”

He’d tried traditional training days in the past, but they didn’t stick:

“You go to a day of sales training, and the next day, it’s forgotten. It’s not retained. We needed something different — something embedded and consistent.”

🧠 From Founder-Coached to Professionally Coached

John turned to MySalesCoach to complement his internal efforts, give his team dedicated development time, and free up his own bandwidth — without compromising quality.

“It’s like when a parent tries to teach their kid to drive — it’s not always effective. Sometimes you need someone external with a clear, objective lens.”

He didn’t want to hire a full-time sales enablement leader. What he needed was flexible, embedded support from people he trusted.

“MySalesCoach gave us just that. It’s an easy sell to any CEO: instead of hiring an expensive enablement leader, you get multiple high-quality coaches who know how to get the most out of your reps.”

🚀 Immediate Impact on the Sales Team

John’s experienced team were each matched to their best-matched coach based on their role, goals and skills gaps — and got stuck in right away.

“The team love it. They’re excited to meet with their coach. It’s not a hassle. I regularly get WhatsApps after sessions saying, ‘This was brilliant.’”

“Our one-to-ones are elevated now. I just ask, ‘What are you working on with your coach?’ and they share learnings with each other too.”

The results followed fast. Stronger discovery, sharper qualification, better prospecting.

“Isabel came from a consulting background — wasn’t used to selling software. Her coach helped her level up fast. She said, ‘That was the best call of my life. It’s going to revolutionise what I’m doing.’”

John shared that the team have closed enterprise deals directly off the back of coaching sessions.

🔄 Accountability, Structure and Clarity — Without Micromanagement

What stood out to John most? The consistency of coaching and the accountability it created.

“What MySalesCoach does really well is give people the freedom to come with problems — but then gives them structure, process, and someone who follows up.”

“You can’t blag your way through coaching. You either did the work or you didn’t — and that accountability has changed how my team shows up.”

🧩 Shifting From Generic Training, To Personalised Coaching

Before MySalesCoach, they’d tried sales training and one-off seminars. They just weren’t moving the needle.

“Everyone’s at different stages in their career. MySalesCoach gives personal 1:1 access — without the overhead of hiring someone internally.

We’ve moved budget from generic training into personalised coaching. It complements our internal enablement and just works better.

It’s helped with the non-obvious stuff too:

“Things like time blocking for prospecting, staying accountable, not just talking about what you should do — but giving practical tools to do it.”

🔋 A Motivated, High-Performing Team (Without Draining Leadership Time)

John now spends less time worrying whether his team is developing — and more time focused on leading the business.

“It’s definitely freed up a lot of my time. I feel reassured knowing the team has someone they can turn to.”

“Sometimes they might not want to ask me something because I’m the boss. Coaching gives them a safe space — it’s almost like sales therapy.”

And it’s not just performance — it’s retention too.

“I actually use it as a hiring benefit: ‘We invest in your development through 1:1 coaching.’ Our latest hire was excited about it.”

“I’d hate to think what the team would be like if we didn’t have it.”

The Result of Coaching:

Enterprise deals closed directly off the back of MySalesCoach sessions, driven by sharper messaging, better qualification, and new strategies.
Clear, measurable improvement in discovery calls, outreach, and follow-up — resulting in more high-quality opportunities.
Reps self-selecting coaching areas, accelerating skill growth and confidence in specific, high-impact areas.

Increased collaboration and knowledge sharing across the sales team from diverse coaching inputs.
Coaching used as a recruitment and retention benefit, attracting top talent.
Leadership freed from day-to-day skills coaching to focus on strategy and growth priorities

Closing Bigger Deals, Faster:
How Targeted Coaching Helped Win Enterprise Business

Closing Bigger Deals, Faster:

How Targeted Coaching Helped Win Enterprise Business