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Senior Sales Operations Manager

United States
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.

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.

What You Will Do
  • Process Optimization
    • 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.
  • Sales Insights & Data-Driven Decision Making
    • 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.
  • Sales Tools and Systems Strategy
    • 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

What We’re Looking For
  • 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

More About Guideline
Everyone should have a simple, affordable way to save for retirement. At Guideline, our plans are low cost and highly automated. This makes it easy for companies to offer a valuable benefit—and easy for people to invest in their financial future with confidence.

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. We are always evaluating our pay zones to be as competitive as possible, so keep in mind these may be subject to change in the future.

Please speak with a recruiter for additional information regarding our tier locations and compensation philosophy.
  • Metro+:
    • The base salary range for this position is $157,500-$175,000 annually.
  • Metro:
    • The base salary range for this position is $144,500-$162,000 annually.
  • National:  
    • The base salary range for this position is $144,500-$162,000 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.
 
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Expected Salary Range

$144,500 - $175,000 USD

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

- Sales enablement:  Focused on sales training and content distribution 

- Revenue operations:  Focused on sales and service delivery process optimization across sales, marketing, and customer success functions.

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