Full-Time

Senior Sales Operations Manager

Confirmed live in the last 24 hours

Guideline

Guideline

201-500 employees

Affordable 401(k) and IRA retirement plans

Fintech
Financial Services

Compensation Overview

$144.5k - $175kAnnually

+ Equity (Incentive Stock Options)

Senior

Remote in USA

Category
Customer Success Management
Field Sales
Inside Sales
Strategic Account Management
Sales & Account Management
Required Skills
Tableau
Salesforce
Data Analysis
Requirements
  • 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.
Responsibilities
  • 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

Guideline provides affordable and customizable 401(k) retirement plans and Individual Retirement Accounts (IRAs) for businesses of all sizes, particularly targeting small to medium-sized enterprises and specific sectors like dental practices. Their service includes end-to-end management of retirement plans, which features automatic enrollment, low monthly fees, and compliance testing. As a 3(38) fiduciary, Guideline manages investment options to ensure they benefit employees. The company operates on a subscription model, charging a low monthly fee that covers essential services, with options for additional features like profit sharing and matching. Guideline also offers Guideline Pro, a platform for financial professionals to assist clients in managing retirement plans effectively. The goal of Guideline is to make retirement savings more accessible and affordable, helping more individuals prepare for their financial future.

Company Stage

Series E

Total Funding

$329.8M

Headquarters

San Mateo, California

Founded

2015

Growth & Insights
Headcount

6 month growth

1%

1 year growth

2%

2 year growth

-5%
Simplify Jobs

Simplify's Take

What believers are saying

  • The SECURE Act 2.0 facilitates small businesses offering retirement plans, expanding Guideline's market.
  • Guideline's mobile app launch aligns with the growing demand for mobile-first financial solutions.
  • Increased demand for digital financial services boosts Guideline's digital-first retirement planning tools.

What critics are saying

  • Increased competition from fintech companies may erode Guideline's market share.
  • Reliance on Vanguard for funds poses risks if partnership terms change.
  • Rapid expansion with new products and professionals may lead to operational challenges.

What makes Guideline unique

  • Guideline offers a flat-fee model, contrasting with industry-standard asset-based fees.
  • The company acts as a 3(38) fiduciary, managing investment options for clients.
  • Guideline provides end-to-end retirement plan management, including compliance and participant education.

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Benefits

Flexible vacation policy

Company equity

401(k) with matching contributions

100% paid employee insurance coverage

Annual learning & development stipend

Parental leave

Sabbatical after 5 years of employment