Back to jobs

Sales Manager, Retirement Plan Conversions

United States
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
  • 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 peopleops@guideline.com.

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.

#LI-Remote

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Select...
Select...
Which of these markets do you have professional experience in? *
Select...
Select...
Select...
How did you hear about this opportunity? (select all that apply) *
What size/stage company have you worked at? *

Select any that apply

Select...

 

 
Select...

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Guideline, Inc.’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.