DealMaker is a fast-growing fintech company revolutionizing the capital markets ecosystem with a mission to make online capital raising mainstream. We empower founders, CEOs, and operators to raise capital digitally, both from their own communities and through strategically marketed campaigns. No other platform provides an end-to-end solution like ours—and our track record speaks for itself, with over $2B raised across 1,000+ campaigns. We power the largest online capital raises for customers like EnergyX ($88M), Green Bay Packers ($65M), Miso Robotics ($72M+), Monogram Orthopaedics (Nasdaq:MGRM) and many others, with 3 IPOs in the past year alone. We are quickly expanding our horizons and are seeking talented team members to join us on our journey to transform the global capital market.
Who You Are
You will own day-to-day payables and receivables for a scaling Finance team across multiple entities. That covers expense management, collections, cash application, and month-end reconciliation support. The role starts as a contract with a clear runway to convert to a permanent hire.
It starts hands-on. As we build and deploy automated expense, collections, and cash application workflows, you will move into overseeing those systems and expanding their coverage, growing from operator to a key driver of how AP and AR run.
Profile
Tech-forward finance professional who prioritizes automation over manual processing. Comfortable executing a structured accounting process today, and motivated to progressively reduce manual work by improving and scaling automated workflows. Firm but professional in customer-facing collections conversations, and organized enough to keep high-volume pipelines under control.
What You'll Do
Accounts Payable and Expense Management
Administer Float for daily credit card transaction coding and semi-monthly employee reimbursement reviews
Manage the wellness stipend reimbursement review cycle
Support expense process controls and system integrity
Collections
Run collections on aged AR: outreach, follow-up, payment plan negotiation, and escalation on delinquent accounts
Manage AR reminder workflows and act as primary point of contact for customer payment discussions
Flag at-risk accounts early and support write-off and escalation decisions
Keep clean records of customer communications and payment commitments in HubSpot
Cash Application
Apply incoming cash against open invoices and reconcile against Stripe activity
Investigate and resolve payment discrepancies, short-pays, and misapplied receipts
Keep aging reports current and support internal AR reporting
General Accounting Support
Post basic bank journal entries and support daily bank transaction activity
Support selected U.S. entity balance sheet reconciliations at month-end
Assist audit and tax preparation by pulling system-generated data sets
Cross-Functional Support
Partner with billing and revenue to resolve invoice disputes and confirm terms
Handle billing tickets and internal AR follow-ups
Respond to ad hoc requests from Finance and other stakeholders as priorities shift
Workflow Oversight
As expense, collections, and cash application workflows are automated, take on a review role: monitor system outputs, manage exception queues, resolve escalations, and ensure accuracy and completeness across AP and AR
What Skills You Need
2 to 4 years of experience in AP, AR, collections, cash application, or finance operations, ideally in a high-volume environment
Hands-on experience with both AP and AR processes
Working knowledge of Stripe and how invoice and payment data flows from it
Comfort in cloud-based finance tools (Float, NetSuite, Stripe, Zip or similar)
HubSpot experience (contact and deal records, logging activity, pulling reports)
Advanced Excel or Google Sheets (pivot tables, lookups, comfort with large datasets)
Sharp attention to detail with a bias toward building systems over repeating manual tasks
Ability to prioritize across multiple high-frequency workflows in a fast-paced environment
Comfortable with direct customer contact and firm but professional collections conversations
Nice to Have
NetSuite AR module and cash application experience
Experience with a dedicated collections tool such as Upflow
Exposure to multi-entity accounting
SaaS, fintech, or financial services background
Why This Role
This role consolidates AP and AR responsibilities that currently span multiple team members, so you own the function end-to-end from day one. The opportunity is to improve these workflows, not just maintain them. We expect this hire to automate 50%+ of routine tasks within the first six months, freeing time for higher-value reconciliation and AR work.
We are a small, high-performing team. Your work will be visible; you will have direct exposure to senior finance leadership, and there is a clear path from contract to permanent hire. If you want real impact on how a scaling finance team operates, this is the role.
Founded in 2018 by leading capital markets lawyers, DealMaker has blazed its own trail as the leading online capital-raising platform.As a tech startup, we are well-capitalized, firmly established in our market, and ready to scale. Here’s why you should want to join us:
Competitive compensation with the opportunity to earn equity—get into a growth company on the ground floor
A diverse & distributed team of doers, innovators, and experts
Shared employee benefit plan (medical, vision, & dental)
We love AI and have tools to support you build innovative solutions
Annual learning support And more!
We use automated and artificial intelligence-based tools (“Automated Employment Decision Tools”) to assist in screening, assessing, or evaluating candidates. These tools may assess job-related qualifications such as skills, experience, and work history. AI-assisted tools support our recruitment team and do not replace human judgment; all final hiring decisions are made by human reviewers.
Applicants may request information about the use of these tools or request an alternative selection process by contacting us at Talent@dealmaker.tech. For more information about how personal information is collected and used, please see our Privacy Notice.
Equal Employment Opportunity
DealMaker does not discriminate in hiring or terms and conditions of employment because of an individual’s race, ancestry, colour, place of origin, religion, gender, gender identity, national origin, citizenship, age, disability, sexual orientation, family status or marital status, or any other protected category recognized by provincial or federal laws.
Please inform us if you require any accommodation, and we will work with you to meet your accessibility needs. For any accessibility-related assistance, requests for information in accessible alternative formats or to report any accessibility problems, please share in your application.