Finance Associate - AR

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

DealMaker is looking for a Finance Associate to own accounts receivable collections and cash application. You'll be the primary point of contact for customer payment discussions, keep our AR process clean and current, and build the habits and systems that let this function scale as it automates.

What You'll Do

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

• Maintain clean, organized records of customer communications and payment commitments in HubSpot

Cash Application

• Apply incoming cash accurately 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

Cross-Functional Support

• Partner with the billing and revenue side to resolve invoice disputes and confirm terms

• Handle billing tickets and internal AR follow-ups

Workflow Oversight

• As collections and cash application workflows are automated over time, take on a review role: monitor system outputs, manage exception queues, resolve escalations, and ensure accuracy and completeness across the AR process

What Skills You'll Need

• 1-2 years of experience in AR, collections, or cash application, ideally in a high-volume environment

• Working knowledge of Stripe and how invoice and payment data flows from it

• 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

NOTE: This will be a 3-month contract 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 [email protected]. 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.