Head of Sales Enablement, Guideline
$160-220k
+ Incentive Stock Options
Retirement plans for small business
Be an early applicant
Retirement plans for small business
201-500 employees
Be an early applicant
$160-220k
+ Incentive Stock Options
201-500 employees
Company mission
To help everyone arrive at a secure retirement.
Role
Who you are
- 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
What the job involves
- 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
- 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
Our take
When businesses offer a 401(K) plan, a message is sent to employees and potential employees that their future is valued by their employer. However, small businesses are often left behind, being charged extortionate fees or ignored by 401(K) providers altogether, leaving many American families with no retirement savings and the potential of retiring into poverty.
Guideline spotted this oversight as an opportunity to jump in and offer small businesses an affordable 401(K). It generates income by charging each business a flat monthly fee per participant.
The company now manages retirement plans for hundreds of thousands of people in over 40,000 companies and has accumulated over $8 billion in assets under management. Benefits providers Intuit, Gusto, and Square all use Guideline as their 401(K) partner.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Company
Employee endorsements
Nice people
"The people at Guideline are really nice, friendly, and helpful. We get to know other members a little better outside of work, and there is an effort..."
Funding (last 2 of 6 rounds)
Jun 2021
$200m
SERIES E
Jul 2020
$80m
SERIES D
Total funding: $339m
Company benefits
- Comprehensive medical, dental and vision plans—100% for employees, 70% for dependents
- Generous 401(k) match
- Paid time off + unlimited vacation days
- Paid parental leave
- Mental health coaching and therapy
- Learning and development stipend
- Cash referral bonus
- Commuter benefits
Company HQ
South San Mateo, San Mateo, CA
Articles
Leadership
Kevin Busque
(CEO)Majored in Computer Information Science at Fitchburg State University. Started out as an Advisory Unix Systems Administrator at IBM and then founded LinkedUp.net, an Open Source consulting company, in 1996. Acted as Chief Information Security Officer at the Institute for Health Metrics and was Director of IT at Humedica. Co-founded TaskRabbit in 2008, acting as its VP of Technology until 2015.
Mike Nelson
(CTO)Majored in Mechanical Engineering at the University of Southern Maine. Was Mobile Developer and CTO at TechStars-backed Accelgolf from 2007 to 2010. Joined SkillSlate as Rails Engineer and CTO, before being hired by TaskRabbit as Staff Engineer in 2012.
Jeremy Caballero
(CPO)Started out as a Junior Programmer at Mail Boxes Etc. Worked as a Photographer and Videographer from 2007 to 2011, and then as a Freelance Digital Designer. Was Lead Designer at lifestyle adventure brand Targa Trophy before joining TargetSafety's UX team. Was made Lead Product Designer at TaskRabbit in 2012.
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