Head of Mid-Market Sales and Business Development, Gusto
$212-307k
OTE
With a 60/40 split between base salary and target commission. Salary range dependent on location
More information about location
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
$212-307k
OTE
With a 60/40 split between base salary and target commission. Salary range dependent on location
More information about location
1001+ employees
Company mission
To create a world where work empowers a better life.
Role
Who you are
- Minimum 10 years relevant sales experience with 7+ years managing sales teams
- Track record growing sales-led businesses in a leadership position including specific contributions and responsibilities for sales talent, tactics, and performance
- High energy, high integrity. Able to motivate and inspire with a track record of building high-performance team cultures
- Proven ability to build a pipeline and achieve revenue targets in a predictable way
- Mathematical mindset with an orientation on repeatability. Excellent at using data to solve problems and drive decision making
- Passion for achieving impact and results that is driven by an entrepreneurial mindset
- A strong communicator (both written and verbal); strong social selling and persuasion skills
- Adaptable sales leader who can upskill teams to deeply penetrate existing partnerships ranging from small to Mid-Market accounts
- Authentic passion for Gusto’s mission and the impact we can have on the world
What the job involves
- Gusto is seeking an experienced Sales Leader with a proven track record in direct sales leadership to drive revenue growth and scale our Direct Dedicated (Mid-Market) Sales organization
- This leader will be responsible for developing and executing strategies that enhance customer acquisition, retention, and expansion through our direct sales channel
- The Head of Direct Dedicated Sales will oversee a team of Account Executives and Business Development Representatives across the Mid-Market and Dedicated sales segments in the direct sales channel focused on building strong customer relationships and maximizing revenue opportunities
- This role reports into the Head of Subscription Sales, who is empowered by the Head of Revenue (external: Chief Revenue Officer)
- The team will have 2 sales teams, a Mid-Market / Dedicated Sales team of 11 Account Executives and a Business Development team of (1 PE, 7 Business Development Representatives). The team on day 1 will have approximately 18 team members
- Set and execute the strategic vision for the Direct Dedicated Sales team, ensuring alignment with company-wide revenue objectives
- Empowers high performing sales teams (2nd line leader) focused on acquisition of employers
- Oversees all performance, hiring and development on the teams (Account Executives and Business Development Representatives)
- Manages teams to consistent best practices using data, customer empathy, and sales skill
- Sets the tone and facilitates successful change management
- Collaborates seamlessly with strategy and operations and enablement functions
- Speaks authoritatively regarding team performance and opportunities, cross-functionally and to Sales and Revenue leadership
- Beyond simply leading a sales team, identifies winning sales tactics and collaborates with sales strategy and operations, enablement, compensation, the people team, and finance partners to improve sales performance and contribution
- Sweats the numbers daily, assessing what’s working and not, comparing across Account Executives, Business Development Representatives and teams, identifying trends to amplify or course correct, and working with Account Executives and Business Development Representatives to improve performance
- Runs predictable sales forecasting that aims to drive growth and continuous improvement (vs. solely projecting attainment)
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 200,000 customers and a multi-billion dollar valuation. In 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that will see it reach key profitability benchmarks. It continues to consolidate its platform, for example by integrating with OpenComp to grant its users access to the company's Compensation Intelligence Platform.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.1m
Company benefits
- Comprehensive medical, dental, and vision benefits, plus a variety of mental health resources
- Flexible vacation - Gusties are encouraged to take the time off they need to continue doing great work
- Fertility treatments, parental leave, pregnancy termination, caregiving, gender-affirming surgery, hormone treatments, transgender-inclusive services, and more
- If you work at one of our homebases, enjoy food, drinks, and good conversation — on us
- Celebrate 5 or 10 years at Gusto and take a month off to recharge
- Take advantage of internet, phone, commuter, and wellness stipends each month, along with a WFH stipend and cash for anniversaries
Company values
- Embody a service mindset - Never stop advocating for the needs of others
- Dream big, then make it real - Be ambitious. Show and do, rather than tell and talk
- Be proud of the how - Ensure deep integrity in everything you do
- Embrace an ownership mentality - Take initiative to leave things better than you found them
- Debate then commit - Share openly, question respectfully, and once a decision is made, commit fully
Company HQ
Central Waterfront, San Francisco, CA
Articles
Leadership
Joshua Reeves
(CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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