Staff Order to Cash Business Systems Manager

ClickUp

About The Position

At ClickUp, we’re not just building software. We’re architecting the future of work! In a world overwhelmed by work sprawl, we saw a better way. That’s why we created the first truly converged AI workspace, unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI, empowering millions of teams to break free from silos, reclaim their time, and unlock new levels of productivity. At ClickUp, you’ll have the opportunity to learn, use, and pioneer AI in ways that shape not only our product, but the future of work itself. Join us and be part of a bold, innovative team that’s redefining what’s possible! 🚀 About the Role The Staff OTC Business Systems Manager owns the vision, roadmap, and delivery of GTM systems and processes for Order‑to‑Cash (OTC) as an individual contributor at the intersection of Sales, PLG, Pricing & Packaging, Deal Desk, Finance, Legal, and GTM Engineering (80% strategy/analysis, 20% hands‑on). Your immediate mandate is to simplify and modernize quoting and approvals, lead the transition from Salesforce CPQ to DealHub, and build scalable processes for a high‑growth PLG SaaS business as the primary interface between GTM stakeholders and engineering across Salesforce, DealHub, Ironclad, NetSuite, Outreach, Gong, ZoomInfo, and related tools. The role is 80% strategy/analysis, 20% hands‑on. Hands‑on work may include detailed requirements, solution design, UAT, and light configuration in Salesforce/DealHub.

Requirements

6–10+ years in systems management, internal tools/product, or business systems product ownership in high‑growth B2B SaaS with both PLG and sales‑assisted motions (e.g., self‑serve sign‑ups, PQLs, expansions).
Prior work with GTM and/or finance‑adjacent systems, including Salesforce and a CPQ platform (Salesforce CPQ, DealHub, or similar) plus exposure to ERP/billing (e.g., NetSuite).
Demonstrated success simplifying complex quoting, approval, or O2C workflows in a fast‑paced environment with frequently changing pricing and packaging.
Strong understanding of SaaS GTM and OTC (quoting, discounting, approvals, contracting, billing models, renewals, amendments, expansions) and how PLG funnels, self‑serve subscriptions, and in‑product upgrades connect to CRM, CPQ, billing, and revenue reporting.
Comfortable working with system concepts such as data models, integrations, and APIs, and collaborating closely with engineers and architects to make pragmatic trade‑offs.
Ability to analyze data (e.g., funnel metrics, cycle times, error rates, conversion by motion) to drive prioritization and measure impact.
Proven track record owning a roadmap and driving cross‑functional alignment across Sales, Growth/PLG, Pricing & Packaging, Deal Desk, Finance, Legal, and Engineering.
Exceptional written and verbal communication, with the ability to clearly explain complex systems and trade‑offs to both executive and frontline audiences.
Strong influencing skills and executive presence; able to align senior stakeholders on priorities and path forward without direct authority.
Bias for action and comfort with ambiguity; you bring structure to messy problem spaces and move initiatives forward.
User‑obsessed mindset with a strong sense of ownership over the seller, approver, and internal stakeholder experience.
High standards for quality and control, balanced with pragmatism and an iterative approach to shipping improvements.

Responsibilities

Own the Vision: Define the end-to-end future state for OTC, mapping how deals progress from product-led trials to sales-assisted enterprise contracts.
Drive Prioritization: Maintain a transparent multi-quarter roadmap that balances quick wins with foundational investments in DealHub, Salesforce, and internal tooling.
Manage Delivery: Partner with GTM Engineering to scope initiatives, plan sprints, and manage delivery from discovery through UAT and launch.
Serve as the Primary Interface: Act as the main point of contact for Sales, Deal Desk, Finance, and Legal to capture requirements and triage systemic execution issues.
Lead Discovery: Conduct structured discovery to identify pain points in quoting and approvals, translating complex pricing changes into scalable system designs.
Drive Change Management: Own the rollout of new processes, including stakeholder alignment, communication plans.
Lead the CPQ Transition: Spearhead the product side of the migration from Salesforce CPQ to DealHub, ensuring a seamless transition for revenue teams.
Simplify Complexity: Redesign deal approval and quoting experiences to reduce cycle time while preserving necessary financial guardrails and controls.
Ensure Cohesion: Define configuration principles that maintain data quality and workflow integrity across the stack (Ironclad, NetSuite, Gong, ZoomInfo).
Automate Workflows: Identify and prioritize opportunities to automate approvals, quote generation, and billing handoffs to reduce manual errors.
Leverage AI: Collaborate on AI-assisted experiences (guided selling, smart approvals) to support both PLG and sales-assisted motions.
Measure & Iterate: Define key metrics (quote-to-close time, error rates) and use data to continuously refine processes, ensuring they meet audit and financial control requirements.