Regional Enterprise Sales Director - West (PST + MST)

Lively
United States
RemoteCareer-pivot friendly

Who this role is best for

Geared toward enterprise sales professionals comfortable with consultative selling and channel relationship-building, with a preference for candidates in the PST or MST time zones who can manage both transactional and solutions-oriented sales approaches.

Best fit for

  • Candidates with a background in selling through benefits brokers and a history of exceeding sales quotas.
    — “Proven track record of meeting or exceeding quota and outperforming activity metrics”
  • Individuals experienced in mapping out decision-makers and managing complex sales processes.
    — “Understands how to map out influencers and decision-makers and handle complex selling through the sales process”
  • Sales professionals who can adapt between transactional and solutions-oriented approaches.
    — “This role is a mix of transactional and solutions-oriented sales motions, so the ideal candidate must be able to adapt based on the prospect.”

Things to consider

  • Must be located in the PST or MST time zone to qualify for the role.
    — “The candidate must be located in the PST or MST time zone.”
  • Requires a strong ability to work with benefits consultants and brokers.
    — “Coordinate with an employer prospect’s benefits consultants to create win-win solutions”

How to stand out

  • Emphasize experience in consultative selling and employer healthcare cost reduction strategies.
    — “Educate and guide prospects through the buyer’s journey to help them learn how Lively can drive healthcare cost reduction to their company”
  • Highlight your ability to partner with internal departments to execute sales strategies.
    — “Partner with marketing and product departments to execute sales strategy as the company introduces enhancements to existing solutions and/or releases new products”
  • Demonstrate your proficiency with sales automation tools like Salesforce, Gong, and BenefitsFlow.
    — “Must be proficient in Salesforce CRM, as well as other sales automation softwares to support a modern sales approach (Gong, BenefitsFlow)”
Pace · Fast PacedCollaboration · HighAutonomy · MediumDecision Impact · Team

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • identified and sourced employer prospects
  • closed good-fit employer prospects
Typical background
benefits solutions sales experience

Skills & requirements

Required

Benefits Solutions SalesConsultative SellingBroker RelationshipsDecision-maker MappingSales Strategies

Preferred

HSA, FSA, HRA, Lifestyle Spending Accounts, Commuter, Cobra

Stack & domain

SalesBenefits SolutionsHSAFSAHRALifestyle Spending AccountsCommuterCobraConsultative SellingNegotiationContract ManagementCustomer EngagementEnterprise SalesBenefits

About the role

Original posting from Lively via Greenhouse

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 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. The candidate must be located in the PST or MST time zone.

Job Description

We are seeking a driven, ambitious, and intellectually curious Enterprise Regional Sales Director to sell Lively’s benefits solutions (HSA, FSA, HRA, Lifestyle Spending Accounts, Commuter, COBRA and more)! This role is focused on winning employer clients above 3,000 benefits eligible lives driven through benefits brokers and consultants and direct-to-employer through a named accounts strategy. You will identify, source, and close good-fit employer prospects using strong consultative selling skills, and contacting warm inbound leads. You will conduct discovery, online and mobile demos, handle objections, negotiate contracts, and close-win business. You’ll drive self-sourced leads for your pipeline, while also partnering closely with internal stakeholders to achieve team goals.

You will execute on a territory plan to deliver maximum revenue potential. This role is a mix of transactional and solutions-oriented sales motions, so the ideal candidate must be able to adapt based on the prospect.

Responsibilities:

Coordinate with an employer prospect’s benefits consultants to create win-win solutions

Drive new business sales within your territory

Day-to-day management of all sales activity in your assigned territory

Meet or exceed personal sales quotas and activity metrics

Conduct outbound phone and email sales discussions with prospective employee benefits brokers and employers

Educate and guide prospects through the buyer’s journey to help them learn how Lively can drive healthcare cost reduction to their company and drive up employee engagement

Drive sales strategies by developing and expanding employee benefits broker and consultant channel relationships

Map out various decision-makers and influencers needed to close deals, effectively engaging all to win new business for Lively

Follow–up with all generated leads in a timely manner

Conduct outbound activities including phone calls, campaign sequences, and similar for all named accounts

Partner with marketing and product departments to execute sales strategy as the company introduces enhancements to existing solutions and/or releases new products

Provide market feedback to help further refine our ideal customer profile across industries within the employee benefits broker channel

Skills & Experience

5+ years of experience as an account executive in SaaS, HR-tech, or benefits industries; having previously sold through employee benefits brokers

Full-cycle selling from generating opportunities through close-winning business

Proven track record of meeting or exceeding quota and outperforming activity metrics

You are a relentless hunter conducting significant outbound activities including calls, emails, in-person meetings, events, etc. 

Understands how to map out influencers and decision-makers and handle complex selling through the sales process

Must be proficient in Salesforce CRM, as well as other sales automation softwares to support a modern sales approach (Gong, BenefitsFlow)

Working knowledge of health insurance (Consumer Driven Health) or employee benefits is required; previous brokerage and/or consultant experience is a plus

Desire and commitment to do what it takes to be successful in sales

Impeccable presentation skills with the ability to influence and engage various audiences

Experience building out a territory and creating new business opportunities

Highly interpersonal, solutions-oriented, and analytical in nature

Positive outlook and a strong ability to take responsibility for their successes and failures

Ability to communicate with customers in a clear, memorable, and inspirational way

Demonstrated ability to work effectively in a fast-paced, rapidly changing environment

A good sense of humor and a down-to-earth personality. We work hard, have fun, and treat people with respect.

The base salary listed is a range for this position. Actual pay will depend on the candidate’s location and experience.$140,000—$160,000 USDWe 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.

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, lifestyle spending accounts, 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:

https://e-verify.uscis.gov/web/media/resourcesContents/E-Verify_Participation_Poster_ES.pdf

#LI-Remote

Source: Lively careers (Greenhouse)

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