Senior Enterprise Sales Leader — Remote, High-Impact Quota

betterhelpcom; San Jose (CA); Remote; USD 135,000 - 165,000; Full time

Benefits offered by this job

Remote work with in-person bonding

Competitive compensation

Holistic perks program (including free

Excellent health, dental, and vision

401k with employer matching

Teladoc Health benefits

Job summary

BetterHelp is seeking a Senior Manager, Enterprise Sales to own new-business sales across SMB and Mid-Market, building pipeline and closing opportunities. You will prospect, establish trusted relationships with employers, brokers, and consultants, and lead multi-stakeholder deals from discovery to close.

The role blends strategic territory planning with hands-on execution in a remote-friendly setting. You will collaborate cross-functionally with leadership and product teams to tailor solutions

Qualifications

• 8+ years of B2B sales experience
• Experience owning new-business sales cycles and revenue targets within SMB and/or Mid-Market segments
• Direct-to-Employer (D2E) sales experience preferred
• Proven track record of meeting or exceeding bookings or revenue targets
• Experience building relationships with brokers, consultants, and employer decision-makers
• Strong prospecting and business development skills
• Ability to manage complex multi-stakeholder sales cycles
• Independent prioritization of accounts and opportunities

Responsibilities

• Own and deliver against an individual new-business bookings quota across SMB and Mid-Market territory
• Develop and execute territory strategy identifying priority accounts and growth opportunities
• Build and maintain a healthy pipeline through various outbound and inbound channels
• Partner with employers, brokers, consultants, and HR-related organizations
• Own opportunities from discovery through negotiation, contracting and closing
• Lead discovery conversations to understand client needs and buying processes
• Deliver compelling presentations and proposals linking solutions to client needs
• Navigate multiple decision-makers across opportunities of varying size
• Lead pricing discussions, contracts, and RFPs within commercial parameters
• Build relationships across HR and Benefits ecosystem
• Maintain pipeline health, opportunity progression, and CRM accuracy
• Leverage data and market insights to strengthen territory and strategy
• Collaborate with Sales Leadership, Partnerships, Marketing, Product, and other teams
• Share successful approaches and market feedback with the team
• Own opportunities and provide high-quality experience throughout the sales process

Skills

B2B sales

D2E sales

Prospecting

Relationship building

Negotiation

CRM management

Independent work

Cross-functional collaboration

Education

Bachelor's degree

Tools

CRM

Job description

BetterHelp is seeking a Senior Manager, Enterprise Sales to own new-business sales across SMB and Mid-Market, building pipeline and closing opportunities. You will prospect, establish trusted relationships with employers, brokers, and consultants, and lead multi-stakeholder deals from discovery to close.

The role blends strategic territory planning with hands-on execution in a remote-friendly setting. You will collaborate cross-functionally with leadership and product teams to tailor solutions