Work at a Portfolio Company

Sr. Manager, Mid-Market Sales



This job is no longer accepting applications

See open jobs at Lively.
Sales & Business Development
Posted on Friday, November 25, 2022

About Lively

Lively set out to raise the bar on benefit solutions, because we believe no one should have to sacrifice personal wellness for financial wellness. While traditional benefits focus more on transactions and less on the humans using them, Lively harnesses user-centric design and innovative technology to deliver an effortless experience for employers and account holders alike. Our modern HSA is consistently top-rated, and we have since expanded our offerings to provide a full suite of other benefits and services for companies, consumers, and financial institutions.

Lively is a remote-first company, headquartered in San Francisco with employees across the US. Come join us and help make getting the value out of your benefits as simple as it should be.

About the Role

We are seeking an experienced Sales Manager to lead and develop a team of sales professionals selling health-related employee benefits (HSA/FSA) to HR buyers and benefits insurance brokers. You and your team will focus on selling to the Mid-Market (100-1,000) segment, and be responsible for creating a repeatable and successful sales motion that includes prospecting and qualifying to closed-won deals. You will work closely with other leaders to establish and improve our broker channel sales processes, and forecast our sales pipeline.

The ideal candidate will have owned the management of a sales pipeline, forecasting, and led a team that outperforms. You have proven experience selling through benefits brokers, and overseeing sales organizations. Additionally, you have proven experience managing a sales team as part of a growing company, and are excited about the coaching and mentoring that it requires. You display empathy to work with a variety of sales professionals, can manage each sales rep to exceeding quota, and can develop a set of processes to optimize your team’s time. You know the nuanced details of an HSA, FSA, and other employee benefits and are excited to share their value.


  • Hire top talent for your team of sales professionals, including sales development representatives and account executives, to meet and exceed quota
  • Establish and continuously improve sales processes as needed to streamline the collective team’s time
  • Mentor and coach each sales rep to overcome challenges and issues specific to their territories and segments
  • Share best practices across the team to highlight victories and minimize challenges
  • Work closely with Revenue Operations and Marketing for sales education and ongoing training
  • Proactively identify and develop growth opportunities in various markets
  • Create strategies for expansion and lead sales team to execute on those strategies

Skills & Experience:

  • 5+ years of sales-related experience, preferably in an Employee Benefits organization, with at least 3+ years in a sales team people management role
  • Proven track record of leading high performing sales teams and performance management
  • You will have proven success in value selling and you are keen on applying a consultative sales strategy as part of our sales motion
  • Must be adept working in Salesforce.com and comfortable working with a variety of other digital sales and sales management and outreach tools
  • Demonstrated excellence in project management, presentation, and leadership skills
  • Must have demonstrated success working with various stakeholders including complex contract negotiation
  • Must have excellent written and oral communication skills, and ability to effectively influence key decisions makers
  • A good sense of humor and a down-to-earth personality. We work hard, have fun, and treat people with respect
  • Bachelor’s degree from an accredited college or university preferred, but not required

Salary range: $110,000 - $150,000 base + 65% bonus (based on team's performance)

Applicants must be currently authorized to work in the United States on a full-time basis with no sponsorship needed now, or in the future.

The base salary range listed for this position is inclusive of all U.S. States and Washington D.C. Actual pay will depend on the candidate’s location and experience.
$110,000$150,000 USD

We encourage you to apply even if you do not meet all of the qualifications, but feel you would be a good fit for the position. However, you must be located in the United States.

Benefits & Perks

We offer competitive salaries, stock options, medical, dental, vision, life and disability coverage. An HSA with employer contribution, FSA, paid parental leave, medical travel benefits, a 401k plan, flexible vacation policy and more!

At Lively, we believe having diverse teams in which everyone can be their authentic self is key to our success. We encourage people from underrepresented backgrounds to apply. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. Come join us in our mission to help people optimize their healthcare spending, maximize their savings, and better their livelihood!

Lively Inc. participates in the E-Verify program. Learn more about E-Verify here:



This job is no longer accepting applications

See open jobs at Lively.