Director of Business Operations and Systems

Swooped; United States; Remote; USD 146,000 - 206,000; Full time

Benefits offered by this job

Equity compensation

401(k) with 4% match

Paid time off

Parental leave

Home office stipend

Wellness stipend

Medical, dental, vision insurance

Job summary

Swooped is seeking a Director of Business Operations and Systems to optimize revenue systems across Sales, Customer Success, and Deal Desk. Reporting to the SVP of Operations, you will architect systems, own CPQ and Salesforce administration, and lead a small team to improve forecasting and pipeline reporting.

You will drive cross-functional data governance, partner with Finance and Marketing on pricing analyses, and oversee integrations and data quality to enable scalable revenue operations.

Qualifications

• 6+ years of progressive experience in Revenue Operations, Sales Operations, or Business Systems in a B2B SaaS environment.
• 3+ years of team leadership or managerial experience guiding direct reports, including sprint management, task delegation, and mentoring.
• Deep expertise in Salesforce strategy, architecture, complex Flows, and system integration patterns across Sales, Service, and Experience Clouds.
• Hands-on administration experience with CPQ platforms.
• Hands-on experience administering Customer Success platforms (such as Planhat, Gainsight, or ChurnZero) integrated with CRM systems.
• Strong understanding of B2B SaaS financial models and metrics, including ARR, NRR, GRR, logo retention, quote-to-cash processes, and sales capacity modeling.
• Advanced expertise in reporting, dashboard creation, data modeling, and financial system reconciliations (such as Salesforce to Maxio).
• Bachelor's degree in Business, Information Systems, Finance, or equivalent practical experience.

Responsibilities

• Serve as primary operational partner to Sales, Marketing, Finance, and Customer Success leadership, translating business priorities into revenue workflows, territory insights, and go-to-market execution.
• Act as the primary architect and hands-on administrator for Salesforce and CPQ systems, managing flow logic, system availability, data integrity, product catalogs, SKU structures, pricebooks, and Deal Desk approval workflows.
• Architect and maintain bi-directional data integrations and automated workflows across core platforms, including Salesforce, Planhat, LeanData, Maxio, Outreach, Highspot, and ChiliPiper.
• Own revenue operations analytics and reporting, encompassing ARR, NRR, and GRR tracking, renewal and expansion forecasting, pipeline hygiene, and churn analysis.
• Manage Deal Desk operational reviews, order form templates, custom SKU controls, and monthly Salesforce-to-billing reconciliations to support quote-to-cash alignment.
• Partner with Finance and Product Marketing to conduct quarterly pricing and discounting analyses to assess historical trends and margin impact.
• Co-own the business systems roadmap with executive operations leadership, driving structured intake, prioritization, sprint cadences, trade-off evaluations, and release calendars.
• Lead, direct, and mentor a team of two direct reports, managing task delegation, conducting technical flow and code reviews, and expanding internal technical capacity.
• Oversee user access provisioning, security configuration reviews, license management, vendor contracts, renewals, invoice approvals, and systems budget allocations across GTM tools.
• Maintain comprehensive technical documentation, architecture maps, change logs, field libraries, data quality standards, and user training materials.

Skills

Revenue Operations

Sales Operations

Team leadership

Data analytics

Forecasting

Dashboarding

Project management

Education

Bachelor's degree in Business/Info Systems/Finance

Tools

Salesforce CPQ

Planhat

Gainsight

ChurnZero

Maxio

LeanData

Highspot

ChiliPiper

Outreach

Job description

The organization is seeking a Director of Business Operations and Systems to optimize its revenue and business systems ecosystem across Sales, Customer Success, Account Management, Implementation, and Deal Desk. Reporting to the SVP of Operations, this role serves as a strategic systems architect, Revenue Operations (RevOps) partner, and team lead managing two direct reports. The position bridges strategic planning and hands-on execution by designing system architecture, administering core platforms, driving forecasting and pipeline reporting, and leading daily business systems operations.

Key Responsibilities

• Serve as primary operational partner to Sales, Marketing, Finance, and Customer Success leadership, translating business priorities into revenue workflows, territory insights, and go-to-market execution.
• Act as the primary architect and hands-on administrator for Salesforce and CPQ systems, managing flow logic, system availability, data integrity, product catalogs, SKU structures, pricebooks, and Deal Desk approval workflows.
• Architect and maintain bi-directional data integrations and automated workflows across core platforms, including Salesforce, Planhat, LeanData, Maxio, Outreach, Highspot, and ChiliPiper.
• Own revenue operations analytics and reporting, encompassing ARR, NRR, and GRR tracking, renewal and expansion forecasting, pipeline hygiene, and churn analysis.
• Manage Deal Desk operational reviews, order form templates, custom SKU controls, and monthly Salesforce-to-billing reconciliations to support quote-to-cash alignment.
• Partner with Finance and Product Marketing to conduct quarterly pricing and discounting analyses to assess historical trends and margin impact.
• Co-own the business systems roadmap with executive operations leadership, driving structured intake, prioritization, sprint cadences, trade-off evaluations, and release calendars.
• Lead, direct, and mentor a team of two direct reports, managing task delegation, conducting technical flow and code reviews, and expanding internal technical capacity.
• Oversee user access provisioning, security configuration reviews, license management, vendor contracts, renewals, invoice approvals, and systems budget allocations across GTM tools.
• Maintain comprehensive technical documentation, architecture maps, change logs, field libraries, data quality standards, and user training materials.

Key Milestones and Objectives

• First 3 Months: Audit the business systems environment, onboard to the CPQ platform to assume ownership of SKU and pricebook management, establish cross-system data governance standards across CRM, CS, and billing systems, initiate recurring post-sales RevOps reporting, streamline monthly billing reconciliations, and achieve a measurable reduction in quote cycle time or order form errors.
• First 6 Months: Deploy semi-automated renewal and expansion workflows between customer success and CRM platforms, deliver at least three prioritized roadmap projects, reduce custom SKU exception requests by 20% through standardized rules, improve customer platform synchronization accuracy, and decrease lead routing turnaround times.

Required Qualifications

• 6+ years of progressive experience in Revenue Operations, Sales Operations, or Business Systems within a B2B SaaS environment.
• 3+ years of team leadership or managerial experience guiding direct reports, including sprint management, task delegation, technical reviews, and mentoring.
• Deep expertise in Salesforce strategy, architecture, complex Flows, and system integration patterns across Sales, Service, and Experience Clouds.
• Hands-on administration experience with CPQ platforms.
• Hands-on experience administering Customer Success platforms (such as Planhat, Gainsight, or ChurnZero) integrated with CRM systems.
• Strong understanding of B2B SaaS financial models and metrics, including ARR, NRR, GRR, logo retention, quote-to-cash processes, and sales capacity modeling.
• Advanced expertise in reporting, dashboard creation, data modeling, and financial system reconciliations (such as Salesforce to Maxio).
• Bachelor's degree in Business, Information Systems, Finance, or equivalent practical experience.

Preferred Qualifications

• Direct administration experience with Nue CPQ.
• Familiarity with related go-to-market platforms, including Maxio, Planhat, Intercom, Pardot, Outreach, ChiliPiper, LeanData, ZoomInfo, LinkedIn Sales Navigator, Chorus.ai, Gong, 6Sense, and Highspot.
• Experience applying modern AI and automation tools to CRM enrichment and workflow optimization.

Compensation and Benefits

• Annual Base Salary: $146,000-$206,000 USD (final compensation determined by candidate experience and certifications).
• Equity compensation and annual compensation reviews.
• Comprehensive medical, dental, and vision insurance for employees and dependents.
• Retirement 401(k) plan with immediate vesting and a 4% company match.
• Paid time off and paid parental leave.
• Home office stipend and wellness stipend.

Location and Employment Type

• Location: Remote (United States).
• Employment Type: Full time.

Equal Opportunity Employer

The organization is an equal opportunity employer and does not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status.