Health & Benefits Outsourcing Sales Lead

WTW
Boston, MA

Description

Key responsibilities:

  • Execute and effectively lead sales process and be proactive in getting our value proposition in front of key prospects.

  • Stay current on benefits administration competitor offerings and contribute to sales team competitive strategy

  • Lead proposal strategy and pursuit teams by ensuring WTW colleagues are prepared for client meetings and understand the value proposition, meeting messaging, asking effective questions, and encouraging storytelling of our successful client experiences.

  • Promote Outsourcing within the market (internal and external), be visible and viewed as a highly credible and trusted resource. Embrace being the face to the markets and a staunch advocate of the Outsourcing business.

  • Collaborate with key leaders in Outsourcing as well as with other Businesses to build brand awareness and develop Outsourcing sales knowledge among the local markets. Going further and leading the sales strategy and driving outcomes prospect by prospect in your assigned territory.

  • Potentially support the sales process for existing clients if a renewal becomes competitive

  • Maintain Dynamics proactively for proper pipeline management

  • Partner with the appropriate stakeholders in supporting the continuous improvement of sales collateral that successfully represents our WTW and Outsourcing value proposition.

  • Collaborate closely with leadership, sales operations, solutions architects, and the consulting teams in executing on our sales process

  • Be an active participant on the Outsourcing sales team

  • Participate and provide feedback in various initiatives throughout the year. As an example, this might include things like working on a specific marketing piece or technology workstream.

  • Continue to develop content depth and expertise in outsourcing and adjacent consulting topics - primarily health benefit strategy and employee experience consulting topics

Mentor and develop junior team members as needed

Qualifications

Requirements:

  • Senior leader that is well regarded in the market and by colleagues and peers internally

  • 10+ years of outsourcing and/or consulting sales experience - demonstrated ability to successfully lead and collaborate with other very senior thought leaders

  • Working knowledge of health & welfare plan design, administration and the competitive landscape in the health and benefits space

  • Interest and aptitude in keeping abreast of latest developments in administration and outsourcing approaches, adjacent consulting topics and contributing to the development of new tools and approaches

  • Prior and relatively recent experience in leading large complex sales as an individual contributor is required - experience selling benefits administration is a plus

  • Proven ability to establish relationships and work collaboratively with team members in other Lines of Business and at all levels to effectively sell and deliver on client needs

  • An executive presence with polished and well developed written and oral communication skills

  • Strong organization skills and an ability to prioritize and direct many competing projects

  • Knowledge of how WTW operates (Segments, businesses, client management, consulting, marketing, etc.) is a plus

  • Embraces change and can help other people deal with a very dynamic environment

  • Strong business acumen with proven strategic and analytical abilities

  • Availability to travel on an as needed basis which could be quite frequent depending on market demands

Note: Employment-based non-immigrant visa sponsorship and/or assistance is not offered for this specific job opportunity.

This position will remain posted for a minimum of three business days from the date posted or until a sufficient/appropriate candidate slate has been identified.

Compensation

The base salary compensation range being offered for this role is $150,000- $250,000 USD per year. This role is also eligible for an annual short-term incentive bonus.

Company Benefits

WTW provides a competitive benefit package which includes the following (eligibility requirements apply):

  • Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Group Accident, Group Critical Illness, Life Insurance, AD&D, Group Legal, Identify Theft Protection, Wellbeing Program and Work/Life Resources (including Employee Assistance Program)

  • Leave Benefits: Paid Holidays, Annual Paid Time Off (includes paid state/local paid leave where required), Short-Term Disability, Long-Term Disability, Other Leaves (e.g., Bereavement, FMLA, ADA, Jury Duty, Military Leave, and Parental and Adoption Leave), Paid Time Off ( ( Washington State only )

  • Retirement Benefits: Contributory Pension Plan and Savings Plan (401k).

At WTW, we trust you to know your work and the people, tools and environment you need to be successful. The majority of our colleagues work in a "hybrid" style, with a mix of remote, in-person and in- office interactions dependent on the needs of the team, role and clients. Our flexibility is rooted in trust and "hybrid" is not a one-size-fits-all solution.

Base salary range and benefits information for this position are being included in accordance with requirements of various state/local pay transparency legislation. Please note that salaries may vary for different individuals in the same role based on several factors, including but not limited to location of the role, individual competencies, education/professional certifications qualifications/experience, performance in the role and potential for revenue generation (Producer roles only)

We understand flexibility is key to supporting an inclusive and diverse workforce and so we encourage requests for all types of flexible working as well as location-based arrangements. Please speak to your recruiter to discuss more.

Compensation and Benefits

Base salary range and benefits information for this position are being included in accordance with requirements of various state/local pay transparency legislation. Please note that base salaries may vary for different individuals in the same role based on several factors, including but not limited to location of the role, individual competencies, education/professional certifications, qualifications/experience, performance in the role and potential for revenue generation (Producer roles only).

Company Benefits

WTW provides a competitive benefit package which includes the following (eligibility requirements apply):

Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Group Accident, Group Critical Illness, Life Insurance, AD&D, Group Legal, Identify Theft Protection, Wellbeing Program and Work/Life Resources (including Employee Assistance Program)

Leave Benefits: Paid Holidays, Annual Paid Time Off (includes paid state/local paid leave where required), Short-Term Disability, Long-Term Disability, Other Leaves (e.g., Bereavement, FMLA, ADA, Jury Duty, Military Leave, and Parental and Adoption Leave), Paid Time Off ( Washington State or remote only )

Retirement Benefits: Contributory Pension Plan and Savings Plan (401k).

We're committed to equal employment opportunity and provide application, interview and workplace adjustments and accommodations to all applicants. If you foresee any barriers, from the application process through to joining WTW, please email [email protected].

This position will remain posted for a minimum of three business days from the date posted or until sufficient/appropriate candidate slate has been identified.

EOE, including disability/vets

Pursuant to the San Francisco Fair Chance Ordinance and Los Angeles County Fair Chance Ordinance for Employers, we will consider for employment qualified applicants with arrest and conviction records.

Posted 2026-04-09

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