In this Leadership Takeover Session, Jack Choppin – employee number one at GoProposal (now GoProposal by Sage) and long-time head of Client Success – explains how bookkeepers can build confident teams, challenge clients on pricing and create “shock and awe” experiences that drive loyalty and growth. For UK bookkeepers bringing in their first team member, or trying to get braver with fees, this is a practical look at what real client success and culture actually feel like day to day.

Download GoProposal's guide for running impactful client meetings: https://goproposal.com/blog/how-to-keep-your-client-at-the-heart-of-every-meeting-with-the-gloss-method/?UTM_Source=6fb

Jack shares how he joined GoProposal on trust in the people before he fully understood the mission, what it was like to be 50% of the company’s salary bill as the first hire, and how that level of transparency built belief and ownership. He talks about the famous “shock and awe” pack, why they poured huge energy into free trials, and how unscalable, high-touch onboarding helped them spot the right customers and turn them into raving fans long before they put card details in.

You’ll hear how GoProposal built a culture of caring deeply and challenging directly: sending physical packs, pre-branding apps, and offering training calls that didn’t just show people where to click, but helped them feel ready to sit in front of a client and say, “Your price needs to go up.” Jack explains why true client success means challenging beliefs, not just being nice, and why the real measure of success isn’t “do you understand the software?” but “are you willing to have that pricing conversation?”

Jack also talks about the emotional side of building a business from the inside. He describes working with founder James Ashford, carrying the pressure of personal goals (like helping Becky leave her job), and learning not to become an “accidental diminisher” who has all the answers. Instead, he shows how asking team members to bring problems with proposed solutions builds confidence, autonomy and genuine leadership capability – the same mindset bookkeepers can use with both staff and clients.

For practice owners, Jack shares what he learned as GoProposal grew and then moved through acquisition into Sage: how openness around targets builds buy-in rather than fear, where to draw the line between healthy pressure and stress, and how small firms can use their size as an advantage by involving team members closely in the journey. He also talks honestly about self-doubt, fear of getting it wrong, and how focusing on intent rather than outcome helps him act even when confidence feels shaky.

This is essential viewing for bookkeepers who want to move beyond “just doing the work” and build a business where clients, team and founder are all truly invested in the same mission.
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About us
We're Jo and Zoe and we help bookkeepers find clients, make more money and build profitable businesses they love. Find out about working with us in The Bookkeepers' Collective, at: 6figurebookkeeper.com/collective
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Disclaimer
The information contained in The Bookkeepers' Podcast is provided for information purposes only. The contents of The Bookkeepers' Podcast is not intended to amount to advice and you should not rely on any of the contents of the Bookkeepers' Podcast. Professional advice should be obtained before taking or refraining from taking any action as a result of the contents of the Bookkeepers' Podcast. The 6 Figure Bookkeeper Ltd disclaims all liability and responsibility arising from any reliance placed on any of the contents of the Bookkeepers' Podcast.

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