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Saturday, September 6, 2025

Kris Sawford – Strategies for Wellbeing in High-Pressure Financial Environments

The financial services sector presents unique challenges for sales professionals, from complex sales cycles to high-stakes client relationships and demanding targets.

In this insightful interview with Keely Portway, Kris Sawford, Sales Manager at FreeAgent, shares his perspectives on ensuring mental wellbeing while maintaining high performance in sales teams.

From structuring realistic targets to creating supportive team cultures, Kris offers practical advice drawn from several years of experience leading teams in the dynamic accounting software industry.

Key Areas of Discussion with Kris Sawford, Sales Manager at FreeAgent:

  • Structuring ambitious yet achievable targets to prevent burnout and turnover.
  • Maintaining motivation through complex and lengthy financial services sales cycles.
  • Establishing healthy work-life boundaries in an “always on” industry culture.
  • Implementing effective team structures to enhance collaboration and wellbeing.
  • Recognizing early warning signs of mental health struggles and providing support.
  • Adapting workloads during high-pressure periods like financial year-end.
  • Daily and weekly practices to enhance team resilience and productivity.
  • Breaking the stigma around mental health conversations, particularly for men in sales.

About Kris:

Kris Sawford is a Sales Manager at FreeAgent, a provider of accounting and bookkeeping software for micro and small businesses. He manages a team of account managers, SDRs, and ISRs who primarily work with accountancy practices to provide software solutions for their clients.


With seven years at FreeAgent, Kris has witnessed significant transformation in the accounting industry and adapted his leadership approach to meet evolving challenges. He champions mental health awareness in the workplace, sharing his own experiences to create psychologically safe environments for his teams.


Kris is particularly passionate about restructuring traditional sales processes to enhance collaboration, implementing innovative team structures such as the “podular” approach that breaks down silos between different sales roles. His leadership philosophy centres on authentic communication, sustainable work practices, and celebrating incremental progress alongside major wins.


As an advocate for mental health support in high-pressure sales environments, Kris emphasises the importance of leadership vulnerability, empathetic listening, and providing appropriate resources for team members facing challenges.

Kris Sawford – Sales Manager at FreeAgent

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