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About Olly Olly

Ready to roll up your sleeves and help transform local marketing forever? At Olly Olly, we're blending technology and real-world expertise to empower businesses across the U.S. like never before.

We believe small businesses are the backbone of our economy. That's why we're on a mission to provide them with tools, strategies, and insights that help them rank higher, generate high-quality leads, get calls and reviews, and, above all, grow sustainably, without the hassle.

The Olly Olly platform complements our hands-on service perfectly: it's no-nonsense, easy-to-use software that helps local businesses streamline operations and contact management, drive leads, stabilize cash flow and maximize revenue with minimal effort, so they can reclaim their time to focus on what they do best.

Our Vision

We aim to be the ultimate all-in-one platform for small-business growth — where automation, AI, and human expertise work together to deliver consistent, measurable results. We started as an agency and have helped thousands of clients succeed. Today, we're in a pivotal transition to a SaaS-first company, building scalable systems that support high-volume execution without sacrificing quality.

Why We Need You

This is a true Operations role responsible for bringing clarity, structure, and executional rigor to the business. We're hiring an Revenue Operations Manager to build, run, and continually optimize HubSpot and our connected GTM systems as the operational backbone of our revenue engine. This is a hands-on, execution-heavy role. You will spend the majority of your time inside HubSpot and its integrations—configuring workflows, resolving data quality issues, improving lead routing, and supporting sales execution—while helping shape execution plans, sequencing work, and tradeoffs in partnership with leadership. You will lead execution through a small operations team, not simply take orders, ensuring GTM systems operate efficiently, reliably, and at scale.

In partnership with the leadership team, you will provide operational input into GTM strategy and then own its execution—translating direction into clean, scalable, and measurable systems and processes. This role is accountable for ensuring those systems and integrations are reliable and deliver clear business outcomes at scale.

You will report to the VP of Sales Operations, partner closely with Sales, Marketing, and Customer Success leaders, and manage 2+ operations specialists or contractors as we scale. You will design, build and execute cross-functional strategies into clear processes. You will be responsible for managing vendor relationships, overseeing integrations.

You Will Be Working in the Following Environment:

• Leading a small team of operations specialists supporting GTM and internal operations
• Managing internal helpdesk for a ~300-employee organization, in partnership with IT
• Owning the organization-wide HubSpot instance as the GTM system of record
• Sharing ownership of critical systems and integrations—including Jira, telephony, lead
• routing, and the broader GTM tech stack—across native and API-based integrations
• Supporting a high-volume outbound Sales motion with significant daily activity
• Supporting Account Management teams on customer management workflows
• Working closely with Product and Engineering on system processes and data flows
• Supporting cross-functional GTM initiatives from planning through execution
• Providing performance reporting and operational insights to the leadership team

✅ Required Experience for this Role:

We don't expect candidates to have all of the experience listed below, but successful candidates will have deep experience across most of these areas and the ability to learn quickly where gaps exist. 

• Experience managing small teams (2–5+ direct reports)
• Operations experience in fast-paced, high-volume environments supporting large sales and/or support organizations, where teams handle frequent, transactional customer interactions and serve multiple internal stakeholders with competing priorities.
• Expertise with HubSpot, ideally with hands-on administrative ownership
• Expertise with Jira, ideally with hands-on administrative ownership
• Expertise owning and maintaining critical tech stack integrations, such as digital contract software and lead routing tools
• Experience integrating and managing telephony systems at scale (200+ users), including high-volume outbound/inbound dialing, as part of a broader operations stack.
• Hands-on experience building, troubleshooting, and scaling API-driven integrations using platforms such as Make (Integromat) and Zapier, including authentication, data mapping, error handling, and monitoring.
• Working knowledge of APIs and webhooks, including how data flows between systems, common integration failure modes, and how to troubleshoot issues in partnership with engineering.

✅ Added bonus Experience Needed in this Role:

• Working knowledge of JavaScript concepts; hands-on experience is a plus, but at minimum the ability to partner effectively with engineering teams and understand JavaScript-based logic, constraints, and tradeoffs.

• Experience working with Stripe data, or partnering on Stripe integrations, including upcoming implementations related to billing, payments, subscriptions, and revenue reporting.

• An engineering background or formal engineering education is a plus, but not required.

• Experience working in a Sales Operations or Revenue Operations function, with a strong understanding of how to partner with sales leadership to use systems, process, data, and lead routing to improve sales rep performance and productivity.

• Experience partnering with revenue leadership and contributing to broader revenue reporting beyond HubSpot, including connecting detailed sales and customer success activities to longer-term revenue performance and business outcomes.

• Experience with customer segmentation and operating multiple support and service models in parallel (e.g., self-serve, pooled support, and dedicated account ownership), including understanding how systems, routing, and processes differ by segment.

✅ Core Responsibilities:

Operational Ownership & Execution

• Own the execution of cross-functional GTM initiatives end-to-end, from planning through steady-state operation
• Serve as the single point of accountability for operational outcomes, not just implementation
• Translate leadership direction into clear execution plans, sequencing work and making tradeoffs as needed
• Proactively identify breakdowns in process, ownership, data, or execution and drive resolution
• Ensure initiatives ship with defined success metrics, monitoring, and escalation paths

Process Design, Standardization & Governance

• Design, document, and maintain clear, scalable SOPs across GTM and internal operations
• Standardize workflows across teams to reduce ambiguity, errors, and operational friction
• Establish and enforce operational standards, SLAs, and expectations consistently
• Continuously refine processes based on performance data, feedback, and changing business needs

Systems, Tooling & Integrations

• Own and administer core business systems, including HubSpot and related GTM tools
• Oversee critical integrations across the tech stack (e.g., CRM, telephony, lead routing, contracts, billing), including native and API-based integrations
• Ensure systems are reliable, usable, and aligned with real-world team workflows
• Balance speed of execution with data integrity, system stability, and long-term scalability
• Partner with Engineering, Product, and IT to troubleshoot issues and implement system

improvements, Reporting, Insights & Outcomes

• Build and maintain operational and performance reporting for GTM and leadership teams
• Ensure data accurately reflects frontline activity and rolls up into meaningful business insights
• Connect day-to-day sales and customer success actions to broader revenue and performance trends
• Surface risks, bottlenecks, and opportunities proactively using data and system signals

Team Leadership & Cross-Functional Partnership

• Lead and develop a small team of operations specialists and/or contractors
• Prioritize and delegate work to ensure focus on highest-impact initiatives
• Partner closely with Sales, Marketing, Customer Success, Product, Engineering, IT, and Revenue leadership
• Act as a trusted operational partner who enables teams to execute effectively at scale

Who Will Thrive in This Role

This Role is a Strong Fit for Someone Who:

• Enjoys being deeply embedded in GTM systems and takes pride in making them work reliably at scale
• Has operated in fast-paced, high-volume sales or revenue environments and is comfortable juggling competing internal priorities
• Thinks end-to-end about execution, including measurement, monitoring, and iteration after launch
• Is comfortable partnering with sales, marketing, customer success, product, engineering and IT to turn strategy into operational reality
• Enjoys owning complex systems, integrations, and data flows rather than handing them off once implemented
• Can lead a small operations team while remaining hands-on in the tools and systems
• Uses data and system signals to anticipate issues, not just react to them
• Is energized by accountability and measures success by outcomes, not activity or documentation

Who This Role Is Not For:

This role is not a fit for candidates who:

• Prefer defining strategy over executing and operationalizing it
• Want a role focused primarily on planning, roadmapping, or stakeholder alignment without hands-on system ownership
• Are uncomfortable spending significant time inside CRM, integrations, and operational tooling
• Have limited experience supporting high-volume GTM teams or managing frequent, transactional workflows
• Expect narrow scope or clean handoffs rather than shared ownership across systems and teams
• Prefer project-based work with clear endpoints instead of long-term system ownership and accountability
• Are uncomfortable being responsible when systems break, data is messy, or priorities shift quickly

What You'll Love About Working at Olly Olly

• Competitive salary based on experience
• Comprehensive benefits (medical, dental, vision, etc.)
• Generous PTO and paid holidays
• High-impact role at a ~$20M company
• Direct influence on revenue execution
• Leaders who value operations and execution

Diversity and Inclusion at Olly Olly

At Olly Olly, we celebrate differences in background, culture, abilities, and perspectives because diversity drives innovation. Your voice matters here — and your perspective helps shape the future of small-business growth.