Upside Capital Holdings

AI Automation Specialist (Financial/Accounting)

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: TYPE OF WORK

Gig

: WAGE / SALARY

Contract Base - Name your package

: HOURS PER WEEK

40

: DATE UPDATED

Jun 3, 2026

JOB OVERVIEW

AI Automation Specialist

Accounting & Property Management

Engagement: Project-Based (Contract Only)
Location: Fully Remote

About the Role

We're looking for an AI Automation Specialist to streamline and automate our accounting operations on a project basis. You'll design and implement AI-driven workflows that reduce manual data entry, accelerate close cycles, and improve accuracy across our financial and property management systems.

This role sits at the intersection of accounting, software automation, and applied AI—ideal for someone who understands both financial processes and the technologies that optimize them. The work is fully remote, and we're hiring for defined project scopes rather than a full-time position.

Key Responsibilities

* Identify repetitive, error-prone accounting tasks and design automated solutions to eliminate manual work.
* Build and maintain integrations and data flows between QuickBooks Online and ResMan property management software.
* Develop AI-assisted workflows for invoice processing, transaction categorization, reconciliation, accounts payable/receivable, and reporting.
* Automate recurring journal entries, rent rolls, owner statements, and month-end close processes.
* Design and implement custom automations using APIs, Python, TypeScript, and automation platforms such as Zapier, Make, or RPA tools.
* Apply AI technologies, including LLMs, OCR, and document-parsing tools, to extract, validate, and structure financial and property management data.
* Evaluate and select AI models based on performance, accuracy, reliability, and cost efficiency.
* Build AI solutions that optimize both operational effectiveness and API/model usage costs.
* Monitor automated workflows, troubleshoot failures, and continuously improve performance and reliability.
* Collaborate with accounting and property management teams to document processes and train staff on newly implemented systems.
* Ensure all automations maintain data integrity, audit trails, security standards, and compliance with accounting requirements.

Required Qualifications

* Proven experience automating accounting, bookkeeping, finance, or property management workflows.
* Strong hands-on experience with QuickBooks Online, including reporting, workflows, APIs, and integrations.
* Experience working with ResMan property management software or comparable property accounting platforms.
* Solid understanding of accounting fundamentals, including GL, AP/AR, reconciliations, and financial reporting.
* Strong programming skills in Python and/or TypeScript.
* Experience building automations using APIs, scripting, and no-code/low-code platforms.
* Practical experience developing AI-powered business automations using modern LLMs and AI tools.
* Experience working with Claude and other leading AI models.
* Familiarity with OpenRouter and multi-model AI architectures, with the ability to select the most effective model for a given use case.
* Ability to design AI automations that balance performance, reliability, and operational cost efficiency.
* Strong analytical and problem-solving skills with exceptional attention to detail.
* Ability to work independently and deliver project milestones in a fully remote environment.

Preferred Qualifications

* Experience in property management, real estate, multifamily housing, or affordable housing accounting.
* Familiarity with OCR, document intelligence, and invoice-processing technologies.
* Experience with data validation, exception handling, and audit-friendly automation design.
* Understanding of financial data security, compliance, and access-control best practices.
* Experience with OpenAI, Anthropic Claude, Gemini, DeepSeek, Grok, Mistral, or other modern AI platforms.
* Experience building AI agent workflows, multi-step automation pipelines, or AI-assisted accounting systems.
* Accounting degree, bookkeeping certification, or equivalent accounting experience is a plus.

Tools & Technologies

QuickBooks Online · ResMan · Python · TypeScript · API Integrations · Claude · OpenRouter · OpenAI · Gemini · OCR/Document Parsing · AI/LLM Platforms · Zapier · Make · RPA Tools**

What Success Looks Like

By the end of the engagement, you will have:

* Automated several high-volume accounting and property management workflows.
* Reduced manual data entry, processing time, and month-end close cycles.
* Built reliable, auditable integrations between QuickBooks Online and ResMan.
* Implemented AI-powered workflows that improve accuracy while minimizing operating costs.
* Established scalable automation systems that can adapt to future business growth and evolving AI technologies.

SKILL REQUIREMENT

Accounting API Development AI Automation

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Upside Capital Holdings

AI Automation Specialist (Financial/Accounting)

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

WAGE / SALARY

HOURS PER WEEK

DATE UPDATED

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