VP/General Manager, B2B at Headspace

| Santa Monica
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About the VP/General Manager, B2B at Headspace:
Headspace’s B2C business has allowed us to build a member base of 45M+ globally. Our vision is to improve the health and happiness of the world. We spend 90K hours in our lifetime at the workplace, so improving the health and happiness of the world means doing so at home and at work. As such, we have built out a B2B business, “Headspace for Work” (HFW) selling into SMB, Mid-Market and Enterprise clients, surpassing 300 customers in 2018. HFW’s mission is to demonstrate how our platform can improve the health, happiness, and productivity of a workforce when implemented into a company’s culture: from absenteeism and presenteeism to hard cost savings on health economics outcomes and increases in productivity. As such, Headspace is now looking for a proven B2B leader to continue driving the company’s expansion through the direct selling and success management of our platform to business customers worldwide. With 300+ customers across segments, we are looking for a leader to guide HFW towards being a covered benefit and well utilized program with MM and Enterprise customers. In our next phase of growth, we are seeking a dynamic and analytical leader to continue to attain and retain top talent and to build our operational playbook to create scalable and predictable revenue.

How your skills and passion will come to life at Headspace:

  • Grow: Attract and retain top talent, building out high performing teams who feel energized and enthusiastic about coming to work every day.
  • Build: Build strategy and prioritization for getting companies to adopt and implement HFW and to expand the relationship, from before the signing of the first partnership to several years ahead.
  • Execute: Build and optimize our B2B/sales model and execute on the strategy. We are expanding the scope of our professional services layer and expect the GM to have a background in the management of technology and services-based approaches.
  • Test, Experiment & Operationalize: Implement the right plan and systems when it comes to account and market segmentation, B2B/sales strategy and ramp time/sales cycle, account handoff, CRM, GTM, comp plans, demand gen, qualification, etc.
  • Partner: Work cross-functionally with Content, Product, Marketing, Engineering, Design, Comms, Finance & Legal.
  • Listen: Listen closely to current and potential customers about what product requests they have, and share this market feedback with product, engineering, and design to help define new products and features and steer long term planning.
  • Prove: Collaborate closely with Headspace’s science team to ensure we take an outcomes-based approach to implementation of HFW and partner with Headspace’s health team to align the HFW strategy with our expansion into healthcare.
  • Plan: Assess list of long term needs and requirements to help ensure the successful evolution of the Headspace enterprise product roadmap.

More specifically:

  • Recruiting & Development: Attract, hire, structure, and retain a growing sales and professional services organization over the next several years.. Foster a culture that is high performance, collaborative, and fun.
  • Strategy and Playbook: In collaboration with product and marketing leadership, develop and implement B2B/Sales strategies that achieve and sustain targeted growth across verticals, user segments, and use cases. Spearhead the development and refinement of the Headspace B2B/Sales playbook.
  • Data-Driven Management: Ensure consistency with Headspace’s leadership culture by taking a data-driven approach to operational reviews, strategy discussions, customer feedback, and all aspects of the role.
  • Onboarding, Coaching, and Mentoring: Enable the B2B teams to qualify and close deals effectively through an efficient and reliable new hire ramp; ensure that new hires are set up for success and optimizes to full potential quickly.
  • Leadership: Be the “cultural leader” of the B2B organization. Participate in major deals. Engage with the team frequently, support their needs. Provide the essential tools and training.
  • High Velocity Acquisition: Create processes and systems that keep pace with the top of the funnel at Headspace. Work closely with the Head of Growth to ensure that Sales/Growth are aligned and a well-oiled customer acquisition machine.
    Strong candidates will have the following essential background characteristics:
  • Experience selling Health & Wellness focused SaaS and/or cloud-based services through a high velocity, inside sales oriented approach; knowledge of how SaaS is sold to LoB leaders, including “land-and-expand” strategies.
  • Significant B2B/Sales leadership experience with a reputation as a top performer; demonstrated success at the VP+ level in a growth stage technology company.
  • Knowledge of corporate HR and Wellness programs and selling benefits into self insured employers is a must.
  • Team building; proven ability to attract and successfully manage superstar caliber reps and managers. Ideally has grown a sales team from 5 to 100+
  • Proven ability to scale a B2B/Sales organization and ramp revenue. Has built infrastructure and operations in a high growth environment (metrics driven; pipeline management; contract development; comp plans, pilot experimentation etc)
  • Metrics oriented; relies on data and analytics to understand sales pipeline, conversion rates, and overall measure and impact results.
  • Experience working collaboratively with marketing to optimize demand generation and has led qualification programs and operations; comfortable working with very high lead volumes.
  • Experience managing distributed teams is required, global experience is considered a plus.Experience in early stage, rapid growth environments is highly preferred.
  • Must be fully comfortable with every aspect of the B2B/Sales cycle, from identifying leads to writing term sheets, negotiating contracts, closing, and transitioning the relationship to account management.
  • Resonance with Headspace’s mission to improve the health and happiness of the world. A belief in what we’re setting out to achieve.
  • Modern, data-driven B2B leader. Quintessential attribute needed to fit into the Headspace culture.
  • Leads from the front; willing to go the extra mile to win a customer. Enjoys coaching and developing upcoming talent.
  • Charismatic and positive attitude with natural leadership qualities.
  • A proactive, hands-on individual able to build & nurture respect of the entire organization through leadership, intelligence, creativity, hard work, and presence.
  • Entrepreneurial, startup “DNA;” comfortable with risks, gutsy, not timid. Ability to be effective in a dynamic, fast paced environment with few resources and significant ambiguity.
  • High level of energy, dedication, and an unrelenting drive to succeed and win.
  • Team player. Track record of building positive relationships with peers and others within a company.
  • Thoughtful listener and communicator; proven ability to gather and use customer/market input to improve existing programs and make adjustments.
  • Unquestionable integrity, credibility, and character; demonstrated high moral and ethical behavior.

How to get started:
If you’re excited by the idea of seeing yourself in this role at Headspace, please apply with your CV and a cover letter that best expresses your interest and unique qualifications.

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Technology we use

  • Engineering
    • JavaLanguages
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    • SwiftLanguages
    • MicroservicesLanguages
    • TypescriptLanguages
    • ReactLibraries
    • Node.jsFrameworks
    • MySQLDatabases


We're located in the heart of Santa Monica on Michigan + Cloverfield, just off the 10 freeway. Bergamont train station is right behind our office.

What are Headspace Perks + Benefits

Headspace Benefits Overview

Unlimited Time Off
Lifetime Headspace Subscription
$500/year learning and development budget
$75 gym stipend
Daily catered lunch and fully stocked fridge
Full Medical, Dental, Vision Coverage
Voluntary Coverage
Basic Life AD&D
Flexible Spending Account
Commuter Benefit

Volunteer in local community
Eat lunch together
Open office floor plan
Unconscious bias training
Health Insurance & Wellness Benefits
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
$75 gym stipend each month
Retirement & Stock Options Benefits
Company Equity
Child Care & Parental Leave Benefits
Flexible Work Schedule
Vacation & Time Off Benefits
Unlimited Vacation Policy
Unlimited Paid Time Off Poilicy
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Free Daily Meals
Stocked Kitchen
Some Meals Provided
Happy Hours
Relocation Assistance
Fitness Subsidies
Professional Development Benefits
Job Training & Conferences
$500 Conference budget
Tuition Reimbursement
Diversity Program

Additional Perks + Benefits

Annual Hackathons. Optional group meditations daily. Competitive salaries. Unlimited PTO. Daily catered lunch.

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