Our part-time CSO helped this benefits and services company in rebuilding their sales function, and align the IT and commercial departments to work towards a more profitable future.

Company Profile

This company specialises in benefits and services aimed at enhancing employee health, well-being, and engagement. Their solutions range from insurance cash plans, an employee benefits platform, technology salary sacrifice solutions, to pay and reward consultancy services. Operating in both the Business to Business (SAAS benefits/Pay and Reward Consulting) and Business to Consumer (Technology Salary Sacrifice/Insurance) sectors, they are at the forefront of sales strategy redesign.

CEO’s Mission

The CEO recognised the need for rebuilding the sales function after observing that the senior leadership team was fragmented. There were evident relationship strains between the two commercial sales environments and the IT function. Following the departure of two of the company’s largest clients, two data breaches, and a key supply partner’s reluctance to collaborate, it was clear that a sales director transformation was imperative. The business required innovative thinking, a new direction, and a bridge between the three departments. Appointing an experienced Commercial Leader would infuse the team with external expertise and novel perspectives, essential for fractional leadership in Sales.

CSO’s Objectives

  • Assume responsibility for the daily management of the commercial operations, overseeing 50 insurance salespeople and 18 account managers.
  • Sales process reengineering: Redesign operational reporting and scheduling to facilitate company scaling.
  • Collaborate with the CIO on pivotal business areas, enabling the company to pivot and achieve a benefits services sales boost.
  • Lastly, cultivate a culture of delivery and operational excellence, emphasising the company’s purpose.

What the Sales Leader / CSO Did

  • Offered leadership and strategic insights, emphasising sales leadership methodologies.
  • Then undertook a detailed review of the business’s planning and scheduling operations, uncovering key data and insight issues, and pinpointing operational mismanagement of crucial client sites. This Sales Function Overhaul educated the board on the company’s operations. For years, the business had grown organically at a steady pace. However, recent operational missteps led to significant customer dissatisfaction and departures, which remained concealed from the board and senior leadership team.
  • Successfully negotiated relationship turnarounds with vital internal and external customers, exemplifying Fractional Sales Director Success.
  • Finally, secured a three-year contract and insurance sales access to the group’s largest policy-holding customer, the UK’s most extensive postal service provider. Additionally, they gained access to locations with one of the UK’s largest transport Unions. This move was pivotal in the benefits company sales turnaround. They also mended internal relationships between B2B and B2C sales teams. Finally, laying out a development pathway for junior sales personnel to transition from B2C sales into B2B account management.


Day-to-day management of the business

The Sales Leader was instrumental in fostering a customer-centric culture. This helped promptly identifies daily challenges, successes, and opportunities for clients and their employees. They introduced a ‘purposeful’ approach to insurance sales and employee accessibility. This was rooted in the ‘protect the unprotected’ and ‘connect the unconnected’ philosophy. This strategy, combined with a significant ‘donation’ to a lapsed policyholder, amplified the company’s value proposition, making the company’s purpose tangible for all employees.

The Results

The Sales Leader created an environment for growth, change and success: 

  • Rebuilt internal relationships across senior leaders and middle managers. 
  • Defused a customer-wide data breach affecting 180 customers. 
  • Maintained 600 payroll slot relationships. 
  • Delivered SaaS turnkey solutions to the group’s largest client.