Sales Manager, Retirement Plan Conversions

As the Manager of the Conversion Team, you will oversee a team of 6-8 AEs who focus on managing complex sales motions and guiding businesses through the process of transitioning their 401(k) plans to our platform. You will collaborate cross-functionally with Legal and Compliance, Marketing, and Partner teams to ensure a seamless conversion experience for clients.
This role requires a combination of strong team leadership, competitive selling expertise, and the ability to mature and scale the organization to meet growing demand.
Key Responsibilities

• Team Leadership & Development
• Manage, coach, and mentor a team of 6-8 professionals responsible for medium to large deal conversions.
• Foster a collaborative, high-performance culture focused on delivering exceptional client experiences and exceeding sales and conversion targets.
• Develop team members’ skills in consultative selling, competitive positioning, and client relationship management.
• Client Engagement & Competitive Selling
• Lead by example in competitive selling, helping the team position our 401(k) software as the best solution for prospective clients.
• Build trust and rapport with decision-makers (HR, finance leaders, executives) to address concerns and overcome objections during the sales and conversion process.
• Develop tailored strategies to help businesses switch their 401(k) plans, highlighting competitive advantages and ROI.
• Cross-Functional Collaboration
• Partner with Legal and Compliance teams to ensure all 401(k) plan transitions meet regulatory requirements.
• Work with Marketing to create competitive positioning materials, case studies, and sales enablement resources that support the team’s efforts.
• Collaborate with Partner teams to develop and execute co-selling strategies with financial advisors, third-party administrators (TPAs), and other stakeholders.
• Operational Excellence
• Build and refine processes to streamline 401(k) plan conversions, ensuring consistency, accuracy, and scalability as the team grows.
• Implement metrics and KPIs to track team performance and identify areas for improvement.
• Act as a key contributor in shaping the organization’s growth strategy and identifying opportunities to improve customer satisfaction and retention.
• Strategic Contributions
• Contribute to the maturity of the conversion organization by identifying gaps in processes, tools, and training, and implementing solutions to drive long-term success.
• Stay informed about industry trends, competitors, and changes in the 401(k) landscape to continuously improve the team’s approach.
• Advocate for client needs internally to influence product enhancements and drive innovation in the platform.

What We’re Looking For

• Experience
• 5-8+ years of experience in B2B SaaS sales, account management, or operations, preferably in the retirement, benefits, or HR technology space.
• Proven success in managing and developing high-performing teams handling medium and large deal cycles.
• Experience with complex sales motions involving multiple stakeholders and decision-makers.
• Skills
• Strong knowledge of 401(k) plans, retirement solutions, or financial services is highly preferred.
• Exceptional competitive selling skills, with the ability to differentiate products and close deals in a highly competitive market.
• Outstanding leadership and team management skills, with a focus on coaching, development, and fostering collaboration.
• Excellent cross-functional collaboration skills, with experience working with Legal, Compliance, Marketing, and external partners.
• Analytical mindset with the ability to use data to drive decision-making and improve team performance.
• Strong communication and presentation skills, with the ability to influence stakeholders at all levels.

Compensation
At Guideline, we believe compensation should be fair and equitable. We take a data-driven approach to set our compensation bands; the successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, and work location.
The expected OTE range for this role is $190,000 - $250,000.
In addition to base salary, this position is eligible for equity in the form of Incentive Stock Options (ISOs).
At Guideline, base salary is just one component of the overall Total Rewards package offered to employees.  All employees are offered comprehensive benefits and perks to help support you and your family.

• Health
• Medical, dental, and vision insurance — We offer multiple plan options with varying company premium contributions
• Opt-out credit for waiving coverage
• Health Savings Account and Flexible Spending Account
• Company paid disability and life insurance
• Optional Voluntary life insurance
• Mental health benefit navigation with Rula for employees and dependents
• Parental Leave
• Paid parental leave for birthing and non-birthing parents
• Generous Time Off
• Flexible time off in addition to company holidays — We observe the NYSE Holiday Calendar
• 401(k) Plan
• We use our own platform and contribute 100% of employee contributions up to 5%
• Other Benefits
• 1-month paid Sabbatical after 5 years of employment
• Annual learning and development stipend — We reimburse approved professional development expenses, up to $750 per employee per year

Guideline provides equal employment opportunities to all employees and applicants for employment without regard to race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.  Additionally, Guideline participates in the E-Verify program in certain locations, as required by law.
Guideline is an equal opportunity employer. Applicants in need of special assistance or accommodation during the interview process can reach out to [email protected].
Guideline is committed to protecting the privacy and security of the personal information of our applicants. Please refer to Guideline's Privacy Policy for information about our privacy and security practices.
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