About Howard Financial

Howard Financial Services is a fractional accounting and CFO firm. We run finance operations for a portfolio of growing companies across hospitality, vacation rentals, professional services, and more. The work spans bookkeeping, controllership, FP&A, and the systems and integrations that make all of it run.

The clients we serve do not look the same. One might run on Toast and QuickBooks Online. The next runs Guesty plus Sage Intacct plus Ramp. A third lives in Streamline with payroll in Rippling. The plumbing between those systems is where things break, and where this role lives.

What this role is

This is a hybrid role: part client operations, part systems integrator. You will own the technical setup of new clients, audit the integrations that already exist on active accounts, and step in when systems are not talking to each other the way they should be.

You will not be writing financial reports or doing the close. You will be the person making sure the data flowing into those reports is clean, complete, and arriving where it needs to. When Toast is not syncing to QBO, when Rippling payroll journal entries are landing in the wrong account, when a property management system is dropping reservations on the way to the GL, you are the first call.

This role sits inside the Business Operations team and works directly with Controllers, the IT Systems Lead, and the founders. The right person is technical enough to read API docs, hit a Postman endpoint, and trace where data is breaking, but operational enough to coordinate the people and timelines around getting it fixed.

What you'll do

Client onboarding (technical setup)

• Own the systems portion of new client onboarding end to end
• Stand up integrations between client tools and our stack: QBO, Sage Intacct, FloQast, Ramp, Rippling, Guesty, Streamline, Toast, and others
• Use APIs, native connectors, and middleware (Zapier, Make, n8n, etc.) to wire systems together
• Document the resulting setup so Controllers and clients know exactly what is connected and how

Integration audits and troubleshooting

• Audit existing client integrations on a recurring basis and on demand when something looks off
• Diagnose sync failures between accounting, payroll, POS, and operational systems
• Read API logs, webhook payloads, and error responses to identify where data is breaking
• Coordinate fixes with vendors, clients, and internal teammates

API work

• Use APIs (Postman, basic scripting, or no-code tools) to pull, push, and reconcile data between systems
• Build lightweight automations to eliminate manual data entry on repeat work
• Partner with the IT Systems Lead on anything that needs deeper engineering

Client-facing coordination

• Run technical kickoff calls with new clients during onboarding
• Translate between client IT/operations contacts and Howard's accounting teams
• Communicate clearly when something is blocked on the client side vs. resolving on ours

Internal operations

• Maintain a clear inventory of every active client's tech stack and integration status
• Flag patterns where multiple clients are hitting the same systems issue so we can productize the fix
• Contribute to internal playbooks for standard onboarding and audit workflows

What we're looking for

Required

• 2+ years in client operations, implementation, technical onboarding, or systems coordination, ideally in professional services or fintech/SaaS
• Hands-on experience working with APIs (Postman, no-code integration tools, or light scripting). You should be comfortable reading API docs, hitting endpoints, and working through authentication
• Real experience with at least one workflow automation tool: Zapier, Make, n8n, Workato, or similar
• Comfort auditing data flows between systems and identifying where things break
• Strong written and verbal communication, especially the ability to explain technical issues to non-technical client contacts
• Self-directed, organized, and comfortable owning a queue of concurrent client projects

Strongly preferred

• Direct experience with one or more of: QuickBooks Online, Sage Intacct, FloQast, Ramp, Rippling, Guesty, Streamline, Toast
• Familiarity with accounting concepts (chart of accounts, journal entries, reconciliations) so you can speak the language of the Controllers you support
• Basic SQL or scripting (Python, JavaScript) for ad hoc data work
• Experience with webhook debugging, CSV transformations, or ETL tooling

Nice to have

• Background in accounting, finance operations, or working inside an outsourced finance team
• Experience writing technical documentation for non-technical users
• Vendor management experience (handling escalations with software providers)

Why this is interesting

You will not be siloed into one product or one client. You will see how dozens of finance operations actually work under the hood, what breaks, and how to make it stop breaking. Finance experience is a plus but not the bar. The bar is strong systems instincts and the ability to figure out integrations on your own.

How to apply

Send a resume and a short note on a system integration you have personally built, fixed, or audited.