The Role

Our commercial team is building a sustainable and scalable enterprise-focused operating model towards complex deal cycles with accounts managing 250m+ revenue and up, including Fortune 500s. This high-ownership role is central to helping improve and harden that model. You will own pipeline visibility, forecast accuracy, GTM process design, and the operational cadence that connects our commercial strategy to daily execution.

You will work directly with the Head of Commercial Sales and serve as the operational backbone for a GTM organization that includes Account Executives, ADRs, Solutions Architects, and Customer Success. This is an individual contributor role with significant scope, direct access to commercial leadership, and clear ownership over outcomes - not just activities.

What You'll Own

Forecasting & Pipeline

• Design and lead a rigorous weekly forecast process built on real data - stage definitions that mean something, deal hygiene standards that hold, and coverage analysis that drives decisions
• Build pipeline reporting that gives leadership a clear, current, and honest view of deal health across the full commercial portfolio
• Proactively surface pipeline risks and opportunities early - not after the quarter is over
• Identify patterns in pipeline data and accelerate variance analysis to sharpen forecast accuracy over time

GTM Process & Playbooks

• Assess current GTM processes across the full sales cycle and drive targeted improvements that increase speed, consistency, and conversion
• Define and operationalize stage entry/exit criteria, cross-functional handoff protocols, and deal desk processes calibrated for complex enterprise transactions
• Partner with Sales, Marketing, CS, and Implementation to ensure process design reflects operational reality - and that it gets followed
• Accelerate playbook development and surface process gaps that manual review would miss

Reporting & Analytics

• Optimize reporting through AI toolsets to reduce time-to-insight and free capacity for higher-order analysis
• Own the commercial reporting layer - pipeline by stage, velocity metrics, win/loss analysis, rep-level performance - and keep it grounded in accurate data
• Translate analytics into clear, decision-ready insights for the Head of Commercial Sales and executive leadership
• Build dashboards in HubSpot and Excel that people actually use to run the business

HubSpot Administration

• Own pipeline configuration, lifecycle stages, automation workflows, and data model integrity in HubSpot
• Proactively identify and close tooling gaps - recommend additions to the GTM stack when the operational case is clear

What We're Looking For

• 5+ years in a Revenue Operations, Sales Operations, or GTM Operations role - ideally in B2B SaaS
• Direct experience supporting enterprise or complex deal cycles requiring multi-stakeholder coordination and longer sales motions
• A track record of taking ownership of GTM operations end-to-end
• Strong HubSpot proficiency across pipeline management, workflow automation, and reporting
• Fluency in AI tools, used as regular practice, not novelty, and with a clear point of view on where they create real leverage in a RevOps context
• Experience with deal desk design, multi-stakeholder deal processes, or contract review workflows
• Advanced Excel skills for analysis, modeling, and reporting
• Operates well as a team of one - thinks strategically, executes hands-on, and holds a high bar for the work regardless of the level of oversight
• Communicates directly and early - surfaces issues when they can still be acted on, not after the fact

Nice to Have

• Experience in compensation plan administration or quota modeling

What to Expect

This role comes with real authority and real accountability. You will not be waiting for direction. You will be identifying what the commercial function needs next and moving toward it. That requires the confidence to make decisions, the discipline to follow them through, and the candor to say clearly when something is not working.

We hold a high bar for the quality of the work and a genuine investment in the people doing it. This is not a role for someone looking to maintain the status quo - it is for someone who finds that kind of work unsatisfying and wants to spend their time on problems that actually matter.
The Benefits of Building with Us

We offer competitive salaries and meaningful equity. We believe everyone on the team should have a stake in what we're building. Benefits vary by region to make sure you're covered in the ways that matter most. In the US, that includes health, dental, vision, life, and disability insurance, plus a 401(k) and flexible spending accounts.

Regardless of where you live, everyone at Ditto can utilize flexible time off. And while we work remotely, our Atlanta and San Francisco offices are open if you ever want a place to work or meet up with teammates.

Apply Anyway

At Ditto, we know game-changers don't always come wrapped in a "perfect" resume. Years of experience? Every single bullet point checked? Meh. That's not what drives us.

What does matter?

• Grit.
• Curiosity.
• Adaptability.
• And a genuine spark for what we're building.

So if you're fired up about our mission but not sure you tick every box - hit that apply button anyway. Use your application to show us how you'll make an impact here.

We're always on the lookout for exceptional humans who want to grow, stretch, and build something meaningful with us.