Bookkeeper

As a Bookkeeper, you'll be the engine that keeps our sales process running smoothly. You'll work cross-functionally with sales, operations, and student success to make sure our pipeline is clean, our paperwork is in order, and our Enrollment Managers can stay focused on converting and supporting prospective students. This is a high-visibility, high-ownership role for someone early in their career who is obsessive about accuracy, consistency, and timely follow-up — and who wants to grow fast.

Deal Administration & Contracts

• Prepare, send, and track client contracts and associated enrollment paperwork through the full signature cycle
• Follow up promptly with clients and Enrollment Managers to ensure agreements are signed and returned before service delivery begins
• Keep and maintain organized records of signed contracts, amendments, and client documentation

Pipeline & CRM Management

• Own day-to-day hygiene and accuracy of our CRM (HubSpot), ensuring contacts, deals, products and tickets are properly maintained.
• Update records consistently and in real time so the team is always working from current information.
• Manage and track the full student inquiry-to-enrollment pipeline, flagging bottlenecks and drop-off points to sales and leadership.

Data Hygiene & Integrity

• Audit CRM records on a recurring cadence: deduplicate contacts, enforce required fields, and clean up stale or malformed data.
• Define and enforce data entry standards so reporting is trustworthy at every level of the funnel.
• Build validation rules, required-field logic, and automated checks that prevent bad data from entering the system. 
• Reconcile CRM data against billing, contract, and enrollment systems to surface and fix discrepancies.
• Maintain documentation of data definitions, field usage, and naming conventions for the broader team.

Payments & Billing Operations

• Manage and reconcile our payment platforms (Stripe and PaySimple) ensuring transactions are accurately recorded as they come in.
• Own the collections process for late or outstanding payments — sending reminders, coordinating with clients, and escalating when necessary.
• Partner with leadership to refine payment policies, installment plan structures, and billing workflows as the business scales.
• Troubleshoot payment failures, disputes, and refund requests in a timely and professional manner.

Reporting & Analytics

• Pull lists, run standard reports, and surface accurate data to sales ops leadership to inform strategy and planning.

Process & Tooling

• Document sales workflows, playbooks, and SOPs as the team scales, and flag opportunities to streamline
• Help evaluate and roll out sales tools and integrations to reduce manual work and improve rep productivity.
• Stay current on CRM features, AI tools, and other tech that can make the team faster.

Cross-functional Collaboration

• Work seamlessly with the sales team: You'll be their go-to partner the moment a deal is posted.
• Partner with operations to ensure handoff processes are seamless and attribution is tracked correctly.
• Coordinate with the student success advising team to align on client issues and resolutions.

Administrative Support

• Handle ongoing data entry and documentation work that keeps records and processes current.
• Support onboarding of new sales ops tooling.

• 2+ years of experience in accounting, bookkeeping, sales operations, revenue operations, business operations, or a related analytical role.
• Impeccable communication skills, written and verbal, both internally and externally — you can move fast, set expectations clearly, and explain a contract, a missing form, or a deadline to a stressed client and leave them feeling supported.
• Demonstrated obsession with clean data: You can describe a data hygiene project you ran end-to-end.
• Hands-on experience or strong comfort with payment platforms such as Stripe and PaySimple.
• Experience managing contracts or deal documentation (e-signature tools like DocuSign or PandaDoc a plus).
• Proficiency in CRM platforms (HubSpot preferred) and comfort with learning new tools quickly.
• Strong Excel/Google Sheets skills; experience with BI tools (Looker, Tableau) is a plus.
• Detail-oriented with a knack for spotting process inefficiencies.
• Excellent organization and follow-through; you do not let tasks fall through the cracks and you build systems so they cannot.
• Comfortable with collections conversations — professional, persistent, and empathetic in follow-ups.
• Self-starter mentality; comfortable with ambiguity in a fast-paced startup environment.
• Curious about new tools and tech (AI, CRM features) that can make your workflows better.
• Genuine interest in education, admissions, or helping students achieve life-changing outcomes.

• Health, dental, and vision benefits
• Direct mentorship from senior leadership
• The chance to build something meaningful in the education space

Salary: $75,000