Senior Sales Operations Manager, Guideline
$144.5-175k
Salary range dependent on candidate location. In addition to base salary, this position is eligible for equity in the form of Incentive Stock Options (ISOs)
Retirement plans for small business
Job no longer available
Retirement plans for small business
201-500 employees
Job no longer available
$144.5-175k
Salary range dependent on candidate location. In addition to base salary, this position is eligible for equity in the form of Incentive Stock Options (ISOs)
201-500 employees
Company mission
To help everyone arrive at a safe, secure retirement, whether they're a small business owner, an employee, or self-employed.
Role
Who you are
- Our ideal candidate has extensive experience delivering sales operations process improvements at a high-growth company, excels in creating scalable solutions that empower sales teams to achieve and surpass their goals, and has a proven track record in managing complex sales commission processes
- The ideal candidate will have a strong understanding of revenue-generating activities and be adept at implementing innovative solutions to unlock efficiencies, improve accuracy, and accelerate sales results
- 5+ years experience in Sales Operations roles; strong preference for candidates with backgrounds in early- to growth-stage SaaS environments
- Proven track record in building relationships and effectively communicating with senior leaders to solve complex, cross-functional challenges in a fast paced, high-growth business environment
- Demonstrated ability to structure complex problems, develop solutions, and craft recommendations and results into easily digestible messages, communications, and executive presentations
- Hands-on experience owning and managing end-to-end sales commission processes, including plan design, calculation, auditing, and reporting. Strong ability to collaborate with Finance and Sales Leadership to create commission structures that balance simplicity, transparency, and strategic alignment
- Advanced Salesforce skills, including system configuration, customizations, workflow automation, and building scalable data architectures. Salesforce Admin or Advanced Admin certification is highly preferred
- Entrepreneurial mindset, with a track record of driving results while navigating constraints in fast-paced, ambiguous environments. Our ideal candidate is resourceful, adaptable, and ready to make a difference by wearing multiple hats
- Skilled in Excel (pivot tables, lookups, arrays, some modeling) and solid understanding of various technologies/tools such as CRM systems (e.g., SFDC) and BI applications (e.g., Tableau) used to optimize and streamline business processes
- Naturally analytical mindset with ability to break down complex issues with limited guidance, operationalize solutions and communicate; just as comfortable in a spreadsheet as a slide deck
What the job involves
- Guideline is seeking a highly experienced and results-oriented Senior Sales Operations Manager to join our fast-paced Revenue Operations team
- This strategic role will shape the future of Sales Operations at Guideline, acting as a key contributor to sales leadership in optimizing processes, enhancing systems, and driving data-driven insights
- Lead transformative improvements to the Salesforce selling journey by developing powerful automations and streamlined workflows to enable greater efficiency and deliver insights that empower Marketing, Partnerships, and Sales Leadership to amplify sales efforts
- Establish predictive frameworks to proactively manage pipeline health, identifying risks, forecasting outcomes, and driving targeted interventions to accelerate high-impact opportunities. Build self-serve systems that allow sales leaders to identify & address challenges swiftly
- Assess and enhance sales processes to eliminate bottlenecks and unlock efficiencies. Drive the adoption of best practices that streamline workflows, minimize friction, and accelerate the sales cycle
- Lead and manage end-to-end sales commission processes, ensuring timely, accurate calculations and reporting. Partner with Finance and Sales Leadership to design commission plans that align with strategic goals and incentivize performance
- Partner with Product, Data Analytics, Commercial Technology, Marketing, and Partnerships to ensure a cohesive go-to-market strategy that aligns with the sales team’s needs. Drive initiatives such as product launches and targeted campaigns within the sales process, ensuring smooth integration and measurable results
- Leverage data to craft compelling stories that highlight trends, uncover new opportunities, and pinpoint areas for improvement
- Collaborate with sales leaders to design KPI dashboards, providing real-time visibility into pipeline health metrics. Develop benchmarks that track individual and team performance, adapting swiftly to evolving business needs to ensure metrics remain relevant, actionable, and aligned with Guideline’s dynamic goals
- Drive accurate sales forecasting by building automated, predictive models that harness historical data to anticipate future trends. Deliver actionable forecasts and insights to sales leadership, enabling strategic planning and resource allocation without the need for manual input from sales teams
- Partner with technical teams to strategically shape and configure Salesforce to be as user-friendly and impactful as possible. This includes building custom workflows, data structures, and automations that help the sales team move faster and stay focused on what matters most.
- Oversee integrations across the sales tech stack to ensure seamless data flow between Salesforce and other tools (e.g., Outreach, ZoomInfo, Gong). Define and manage integration architecture, guaranteeing that data consistency is maintained, while supporting a cohesive end-user experience
- Implement and expand automation capabilities within Salesforce to eliminate repetitive tasks, freeing up sales reps to focus on high-value activities and strategic selling
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) partners.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-6% employee growth in 12 months
Company
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
Downtown, Burlingame, CA
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
(Co-Founder & 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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