Head of Sales

Guideline is seeking a Head of Sales to lead the sales segment, sales leaders and all account executives. This role will report to the Chief Revenue Officer and is available remotely.

What You Will Be Working On

We are looking for a senior sales leader and operator that is a driver of the Guideline business, innovative around sales motions, and systems oriented. This is the perfect opportunity for someone who loves building, leading teams, working with data and iterating on new sales channels.

The ideal candidate is an expert in building Go-To-Market strategy and leading a team to execute with a high level of excellence.

• Lead a growing team of Sales Managers and Account Executives with a focus on professional development and growth through setting clear expectations, coaching, development and feedback
• Drive our systems; build scalable foundations that accelerate our sales team, drive efficiency and make the business faster
• Develop and build new and existing sales channels for Guideline, experimenting and capitalizing on momentum
• Define, report, and continuously improve on team goals and KPIs
• Manage the day-to-day execution of our Sales Managers and Account Executives, ensuring teams meet their quota, activity, and other performance-related goals
• Champion our culture and values, fostering a culture of feedback, growth, and learning, while promoting an environment where team members thrive and excel
• Collaborate with the internal stakeholders and cross-functional partners on the strategic direction of the organization, including providing leadership and insight, influence around product
• Actively participate in executive and senior leadership team meetings and on-site sessions, providing leadership and insight to drive overall business success
• Partner with Chief Revenue Officer, RevOps, Data Teams, and other internal stakeholders to implement GTM strategy, develop roadmaps designed to scale efforts, and improve reporting (inc. KPI, OKR, forecasting)
• Conduct thorough market analysis to identify new opportunities, understand industry trends, and stay ahead of competitors, with a particular focus on State and Federal opportunities

What We’re Looking For

• Expert in sales craft, with demonstrated leadership in scaling and advancing a sales business, ideally in the regulated SaaS or fintech industry
• 5+ years of sales leadership; 2+ years as a second line leader with hands-on experience building high-performing teams of 10+ members, including demonstrated managerial experience with team members from individual contributors to seasoned people managers
• Demonstrated experience successfully executing across multiple lines of ownership and business
• Proven track record carrying a quota for yourself and your team
• Flexible - we’re moving fast, so the ability to constantly adapt to new conditions is a must
• Passionate about technology as well as experience in using technology to deliver prospect solution
• Expertise in utilizing data-driven insights to measure effectiveness and make strategic recommendations; proven ability in financial decision-making, including building ROI business cases to secure funding for sales initiatives
• Demonstrable experience in developing strategic sales plans that comprehensively cover market analysis, customer engagement, and revenue generation

Why Guideline

Our values serve as a compass that guides our decisions and are considered non-negotiable, especially when it comes to hiring. Together with our employees, partners, and customers, we live these values every day.

Everyone has hopes and dreams for the future, but it seems like only some of us are able to financially invest in them. That’s something we’ve made it our mission to solve - to help everyone arrive at a safe, secure retirement. Whatever type of work you choose, whatever the size of your business.

We’ve done this by building the easiest, most affordable, most comprehensive platform for investing in your financial future. It replaces doubt and fear with transparency, knowledge and understanding. It makes it possible, even enjoyable, to participate in a retirement plan as an employer, employee or partner.

Because when you know how to safely, smartly invest today, you’ll be able to do more of what you love when the future arrives. And that is something everyone should be able to look forward to.

Compensation

At Guideline, we believe compensation should be fair and equitable. We take a data-driven approach to set our compensation; the successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, and work location. In addition to base salary, this position is eligible to participate in a sales incentive program and equity in the form of Incentive Stock Options (ISOs). Incentive compensation is not guaranteed.

At Guideline, all employees are offered comprehensive benefits and perks to help support you and your family.

• Flexible time off in addition to company holidays — We observe the NYSE Holiday Calendar
• 401(k) with matching contributions — We use our own platform and match 100% of the first 3% contributed, and 50% of the next 2% (for a max employer contribution of 4%)
• 100% employer-paid healthcare, vision, and dental insurance for employees and 70% coverage for dependents
• Opt-out credit if all three plans are waived
• Eligibility to participate in Health Savings Account and Flexible Spending Accounts
• Disability and life insurance options
• Mental health benefits, including therapy and coaching through Modern Health, for employees and their dependents
• Paid parental leave for birthing and non-birthing parents
• 1 - month Sabbatical after 5 years of employment
• Annual learning and development stipend — We reimburse approved professional development expenses, up to $750 per employee per year.

Guideline provides equal employment opportunities to all employees and applicants for employment without regard to race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. Additionally, Guideline participates in the E-Verify program in certain locations, as required by law.

Guideline is an equal opportunity employer. Applicants in need of special assistance or accommodation during the interview process can reach out to [email protected].

Guideline is committed to protecting the privacy and security of the personal information of our applicants. Please refer to Guideline's Privacy Policy for information about our privacy and security practices.