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Head of Sales Enablement

United States
Be a Part of our Team!
Guideline was founded in 2015 with the mission to help everyone arrive at a secure retirement. We are transforming the retirement industry with more transparency, seamless technology integrations, accessibility and affordability.  
 
We are a fast-growing technology company looking for exceptionally motivated people who love to see their work’s impact daily, are driven to ensure the company’s success, and want to be a part of the next generation of retirement planning.

Position Overview
We’re seeking an experienced Head of Sales Enablement to lead and develop strategies to drive sales success and improve productivity across our sales organization. In this role, you will be responsible for designing, implementing, and optimizing enablement programs that empower our sales team to meet and exceed targets. 
 
You’ll work cross-functionally with sales, marketing, product, and customer success teams to align initiatives that drive results, while ensuring consistent messaging and a strong go-to-market strategy.

You will…
  • Develop and Execute Sales Enablement Strategy: Create a comprehensive enablement roadmap that supports sales teams with tools, training, and resources needed to achieve revenue targets.
  • Sales Training & Development: Design and deliver onboarding and continuous training programs on product and retirement domain knowledge, sales processes, and skills development to improve sales efficiency.
  • Content & Resources Management: Collaborate with marketing to develop and optimize sales content and ensure resources are easily accessible and align with customer journey stages.
  • Performance Measurement: Establish KPIs to measure the effectiveness of enablement programs, track improvements in sales productivity, and adjust strategies accordingly.
  • Cross-Functional Collaboration: Partner with product, customer success, and marketing teams to create sales-focused campaigns, insights, and product updates that empower the sales team.
You Have…
  • 8+ years of experience in Sales Enablement, Sales Training, or a similar role within the SaaS industry.
  • Proven track record of designing and implementing successful enablement programs that drive revenue growth and improve sales effectiveness.
  • Strong understanding of B2B SaaS sales processes, methodologies, and metrics.
  • Exceptional communication, collaboration, and project management skills.
  • Ability to analyze data and present actionable insights to leadership.
  • Familiarity with sales enablement platforms including Gong or basic LMSs is a plus.
 
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 bands; the successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, and work location.
  • The base salary range for this position is $160,000 - $220,000 annually.
In addition to base salary, this position is eligible for equity in the form of Incentive Stock Options (ISOs). 

At Guideline, base salary is just one component of the overall Total Rewards package offered to employees.  All employees are offered comprehensive benefits and perks to help support you and your family.
  • Health
    • Medical, dental, and vision insurance — We offer multiple plan options with varying company premium contributions
      • Opt-out credit for waiving coverage
    • Health Savings Account and Flexible Spending Account
    • Company paid disability and life insurance
    • Optional Voluntary life insurance
    • Mental health benefit navigation with Rula for employees and dependents
  • Parental Leave
    • Paid parental leave for birthing and non-birthing parents
  • Generous Time Off
  • 401(k) Plan
    • We use our own platform and contribute 100% of employee contributions up to 5%
  • Other Benefits
    • 1-month paid 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 peopleops@guideline.com.

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.
 
#LI-Remote

Expected Salary Range

$160,000 - $220,000 USD

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- Sales enablement:  Focused on sales training and content distribution 

- Sales operations: Focused exclusively on process, productivity, and support programs directly impacting the sales organization 

In your Sales Enablement roles, which level(s) of organizational maturity do you have experience working with? *
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