Rev Ops Systems & Data Manager

Overview

You'll run the systems and data operations for ParentSquare's revenue organization, reporting to the Director of Rev Ops. You're managing CRM hygiene, system integrations, dashboard builds, and evaluating new tools as they scale their K-12 school district sales motion. One systems admin reports to you, but most of your time is hands-on building, fixing, and optimizing.

Role Snapshot

Company Context

Stage: Series B+ ($67.8M raised, backed by Serent Capital)

Size: 373 employees

Growth: Growing Rev Ops team again, expanding after recent hires

Market Position: Strong player in K-12 school communication space (4.6/5 on G2 from 333 reviews). Competes with ClassDojo, TalkingPoints, Bloomz, PowerSchool Schoology.

Product: School-to-home communication platform for PreK-12. Districts buy it to replace fragmented communication tools (emails, paper flyers, multiple apps). Includes messaging, forms, payments, website builder.

Customers: School districts and individual schools across the US. Deals range from single schools to entire districts.

GTM Reality

Sales Motion: Mix of inbound (districts looking for communication solutions) and outbound targeting to district admins and superintendents. Sales cycle is tied to school budgets and procurement timelines.

Tech Stack Complexity: You're managing tools for a revenue org that includes inside sales reps, AEs, AMs/CSMs, and leadership. Based on company stage, likely running Salesforce or HubSpot, plus sales engagement tools, BI/dashboards, potentially CPQ for complex district pricing.

Current State: They're hiring to help "rethink how we use existing tools" - translation: things work but aren't optimized. Systems have grown organically as the company scaled. Now they need someone to clean it up and make it scalable.

Competitive Landscape

Main Competitors: ClassDojo (free/freemium, huge user base), TalkingPoints (multilingual focus), Bloomz, PowerSchool Schoology (part of larger SIS)

Differentiation: More comprehensive than point solutions, less overwhelming than full SIS systems. Strong on parent engagement metrics and two-way communication.

Common Objections: Budget constraints in education, existing tools that are "good enough," reluctance to add another platform for parents to learn.

What You'll Actually Do

Time Breakdown

Hands-on System Work (50%) | Data & Reporting (25%) | Strategy & Planning (15%) | Team Management (10%)

Key Activities

• CRM Administration: You're maintaining Salesforce/HubSpot fields, workflows, validation rules. When sales complains data is wrong or a report breaks, you're debugging it. You'll spend time cleaning up duplicates, fixing automation that's breaking, and dealing with integration issues between systems.

• Dashboard & Reporting Builds: Sales leadership wants to see pipeline health, CS wants expansion metrics, execs want forecasts. You're building these in Tableau/Looker/Salesforce dashboards. You'll rebuild the same report multiple ways until stakeholders agree on what they actually want to measure.

• Tool Evaluation & Implementation: They're growing and need to evaluate new tools (maybe rev intelligence, better forecasting, partner tracking). You're doing vendor demos, building business cases, scoping implementations. You'll own the project management when they decide to buy something new.

• Data Integrity Projects: Sales reps don't log activities consistently. Opportunities sit in wrong stages. Account hierarchies are a mess (parent districts vs individual schools creates complexity). You're building processes and automation to improve data quality, and probably nagging people when they don't follow them.

• Cross-functional Problem Solving: Marketing wants better attribution, sales wants territory rules automated, CS wants renewal forecasting. You're the person who figures out if the system can do it, how to build it, or whether they need a new tool.

• Managing Your Direct Report: One systems admin reports to you. You're delegating routine admin tasks, unblocking them when they get stuck, and probably still doing a lot of the complex builds yourself.

The Honest Reality

What's Hard

• Legacy Systems Debt: You're inheriting systems that were set up when the company was smaller. There's technical debt, workarounds that made sense 2 years ago, and probably some "we've always done it that way" resistance when you try to change things.

• Competing Priorities: Sales wants new features, CS needs better dashboards, execs want forecasting accuracy. Everyone thinks their request is urgent. You're constantly triaging and explaining why things take time.

• Data Quality is a Grind: No matter how many rules you build, reps will find ways to enter bad data. You'll spend a lot of time fixing things that shouldn't be broken and enforcing processes that people ignore.

• Ambiguity in "How It Should Work": Stakeholders often don't know exactly what they want until you build it. Expect to iterate a lot and rebuild things when requirements change.

• Limited Resources: You have one direct report. For a 373-person company with growing complexity, that means you're going to be hands-on doing a lot yourself. You won't have a big team to delegate to.

What Success Looks Like

• Reports Actually Get Used: Sales leaders start their week checking your dashboards instead of asking for one-off pulls. Reps trust the data enough to run their business from it.

• Systems Run Smoothly: Fewer "this broke" emergencies. Automation works. Integrations don't randomly fail. You're spending time on improvements, not firefighting.

• Stakeholders Stop Worrying About Tools: Revenue teams trust that systems will support them. They come to you early with needs instead of buying shadow IT solutions.

• Clean Implementations: When you bring on new tools, they actually get adopted and deliver value. No shelfware.

Who You're Supporting

Internal Stakeholders:

• Director of Rev Ops (your manager) - wants strategic partner who can execute
• Sales leadership - needs visibility into pipeline, forecasting, performance
• Sales reps (ISRs and AEs) - want tools that make their jobs easier, not harder
• Customer Success team - needs renewal tracking, expansion visibility, account health data
• Finance - wants accurate revenue data for planning

What They Care About:

• Sales: Can I see my pipeline? Does this tool actually help me sell? Stop making me enter data in multiple places.
• CS: Which accounts are at risk? Where's my expansion opportunity? Is renewal data accurate?
• Leadership: What's our forecast? How's the team performing? What's our CAC/LTV?
• Finance: Numbers need to match. Revenue recognition needs to be clean.

Requirements

• Deep hands-on experience with CRM administration (Salesforce or HubSpot), not just "using" it as a sales rep
• Proven ability to build reports, dashboards, and automation that people actually use
• Track record of implementing new systems or major process changes in a revenue org
• Comfortable challenging existing processes - they want someone who'll say "we should rebuild this, not just patch it"
• Experience managing at least one person, but still willing to be 80%+ IC yourself
• Ability to translate business requirements into technical solutions without a ton of hand-holding
• Bonus: Experience in B2B SaaS selling to education/government (budget cycles, procurement complexity, multi-stakeholder deals)
• Bonus: Worked at a company through a scaling phase (50 → 200+ employees) and dealt with systems that needed to grow up