---
title: 'Financial Controller at DealMaker'
canonical: 'https://feeny.ai/job/financial-controller-dealmaker-toronto-5w2negaxw3wn'
type: 'job'
last_seen: '2026-09-09'
---

# Financial Controller at DealMaker

- **Company:** DealMaker
- **Location:** Toronto, Canada
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-07-31
- **Last confirmed live:** 2026-09-09
- **Apply:** https://jobs.ashbyhq.com/dealmaker/46fa7caa-9c44-4399-a280-292ee69c0deb

## Job description

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 are an experienced accounting leader who thrives on owning the full-cycle accounting function end to end. You bring a detail-oriented, process-driven mindset and have managed accounting operations across multiple entities, currencies, and countries. You have led and developed high-performing teams, and you love building, scaling, and automating systems and controls. You embody our values: prioritizing speed, driving outcomes, pushing limits, finding a way, being bold, innovating, and obsessing over customers.

## WHAT YOU'LL DO

- Own the Accounting Function: Lead accounting and financial reporting, including accounts payable, expense management, and payroll, across our US, Canadian, and international entities.
- Manage the Month-End Close: Own the multi-entity close in NetSuite and FloQast, including reconciliations, journal entries, accruals, intercompany reclasses and eliminations, currency revaluation, and transfer pricing, ensuring transactions are recorded accurately and on time in accordance with US GAAP.
- Deliver Financial Statements & Reporting: Prepare consolidated balance sheets, income statements, and cash flow statements; compile and present preliminary and month-end results to leadership; and support monthly business reviews and board reporting.
- Oversee Payroll: Oversee semi-monthly US and Canadian payroll, monthly Colombia payroll, and contractor payments, ensuring accurate funding, journal entries, review, and approvals.
- Lead Audit & Tax: Manage the annual audit and corporate tax filings, along with HST, SR&ED, and transfer pricing, owning relationships with external auditors and tax advisors.
- Strengthen Controls & Systems: Develop and maintain a strong internal control environment; improve, automate, and scale accounting processes and documentation; and lead system implementations and migrations, such as the move to a new payroll platform.
- Lead & Develop the Team: Provide coaching, training, and guidance to accounting staff and outsourced partners, building a high-performing team.
- Leverage AI: Actively apply AI tools to automate and improve accounting workflows, reporting, and analysis, continuously raising the bar on speed, accuracy, and efficiency.
- Drive Special Projects: Respond to requests for special reporting and finance initiatives by understanding the problem, developing a plan, and executing deliverables.

## WHAT SKILLS YOU NEED

- Accounting Leadership: Demonstrated experience leading an accounting function, including managing, mentoring, and developing a team.
- Multi-Entity Expertise: Experience with complex multi-company, multi-currency, multi-country organizations for consolidations and tax, and with managing transactions and workflows across multiple business units.
- Designation: An accounting designation such as CPA, CGA, CA, or CMA.
- US GAAP: Strong US GAAP experience.
- Payroll: US and Canadian payroll processing experience; ADP, Humi, and/or Rippling experience preferred.
- Systems: Hands-on experience with our stack or comparable tools: NetSuite (ERP), FloQast (close management), Zip (AP), Float (corporate cards and expenses), ADP, Humi, and/or Rippling (payroll), Deel (contractors), and Drivetrain (FP&A); advanced skills in Microsoft Excel and Google Sheets.
- Analytical Acumen: Strong analytical skills with a data-driven approach to managing projects.
- AI Adoption (Required): At DealMaker, AI fluency is a mandatory part of every role. You actively use AI tools to work faster and smarter, and you are committed to continuously building your AI skills as our tools and workflows evolve.
- Bonus: Understanding of crowdfunding and exempt securities under SEC regulations.

Hybrid Flexibility: Work in a hybrid model, 3 days per week in our Toronto office, alongside a highly motivated team.

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.

## About DealMaker

## Company Overview
- **One-liner**: DealMaker provides an all-in-one digital platform that enables companies to raise capital online via Regulation A, Regulation Crowdfunding (CF), and Regulation D offerings, handling everything from investor acquisition to compliance and payments.
- **Entity Type**: Private (multiple venture rounds, latest private equity round in 2024)
- **Headquarters**: New York, New York, United States
- **Founded**: 2018
- **Founders**: Rebecca Kacaba (CEO & Co-Founder)

## Core Business
- **Primary industry**: Financial Services / Capital Markets Technology (Fintech)
- **Target customers**: B2B – growth-stage companies, startups, and established organizations looking to raise capital from retail and institutional investors.
- **Mission/purpose**: Empower founders to raise capital digitally from their own communities and through strategically marketed campaigns, making online capital raising mainstream.

## Products & Services
- **DealMaker Platform (SaaS)**: End-to-end capital raising solution that provides investor acquisition, securities management, fund processing, and investor communications in one system. Acts as a one-stop-shop digital raise platform, transforming the process into a simple eCommerce experience – companies add an “Invest Now” button to their existing site and DealMaker handles compliance, payments, and everything in between.

## Market Standing
- **Valuation/Market Cap**: Not disclosed (privately held)
- **Key Metric**: Annual Revenue of ~$9.0 million (latest estimate); total capital raised for clients exceeds **$2 billion** (including notable clients like Green Bay Packers, Miso Robotics, Monogram Orthopaedics).
- **Notable Investors/Partners**: CIBC Innovation Banking (led venture rounds in 2022 & 2023), The Canadian Securities Exchange (investor in 2022 round), and additional private equity investment (2024).
- **Growth Signals**: Headcount grew 37.9% year-over-year to 143 employees; operates in 8 countries; acquired Rally On Media (2025) and Ridge Growth Agency (2022); active job postings for roles in sales, client strategy, and creative production.

## Competitive Advantages
- **One-stop shop**: Integrates investor acquisition, securities management, compliance, and payments – eliminating the need for multiple vendors.
- **Proven track record**: Helped raise over $2 billion for hundreds of companies, including high-profile names.
- **Simplified user experience**: Capital raising is reduced to a single “Invest Now” button, drastically lowering friction for founders.
- **Regulatory expertise**: Handles complex SEC regulations (Reg A, CF, D) and provides built-in compliance capabilities.

## Strategic Focus
- **Current priorities**: Deepening marketing capabilities (acquisition of Rally On Media), expanding enterprise and partnership sales (Enterprise Account Manager, Director of Client Strategy roles), and growing the technology team to enhance platform features.
- **Direction**: Scaling the platform to serve larger, more complex raises while maintaining the self-serve eCommerce model; increasing international presence (offices in US, Canada, Colombia, Brazil, Nigeria).

## Why Work Here
- **Culture highlights**: The careers page describes an environment where “ideas flow freely, innovation is rewarded, and excellence is the standard.” The team is mission-driven, focused on making capital raising accessible.
- **Location & hybrid policy**: Offices in New York (HQ) and Toronto, with team members across the Americas. Remote/hybrid details not explicitly stated; likely hybrid given multiple office locations.
- **Engineering & team**: Tech stack includes Python, Django, React, Snowflake, dbt, and modern tools. Employees come from companies like Republic, StartEngine, and Strikepoint.
- **Note**: Employee rating on LinkedIn is 2.7/5.0 (61 reviews), with below-average scores in work-life balance (2.1) and culture (2.3) – job seekers may want to investigate further.

## Sources
1. [dealmaker.tech](https://www.dealmaker.tech/)
2. [dealmaker.tech/about-us](https://www.dealmaker.tech/about-us)
3. [linkedin.com/company/dealmakertech](https://www.linkedin.com/company/dealmakertech)
4. [theorg.com/org/dealmaker](https://theorg.com/org/dealmaker)
5. [jobs.ashbyhq.com/dealmaker](https://jobs.ashbyhq.com/dealmaker)

## Other roles at DealMaker

- [Copywriter](https://feeny.ai/job/copywriter-dealmaker-new-york-9c0t0vbhsx40) — New York, NY
- [Senior Data Analyst](https://feeny.ai/job/senior-data-analyst-dealmaker-medellin-pxjds7hz2x3x) — Medellín, Colombia
- [Creative Strategist](https://feeny.ai/job/creative-strategist-dealmaker-los-angeles-06ffsrbp6bwq) — Los Angeles, CA
- [AI GTM Specialist](https://feeny.ai/job/ai-gtm-specialist-dealmaker-toronto-y8sy08hzhxym) — Toronto, Canada
- [Senior Marketing Strategist](https://feeny.ai/job/senior-marketing-strategist-dealmaker-new-york-h4bck3c19891) — New York, NY
- [Content Marketing Manager](https://feeny.ai/job/content-marketing-manager-dealmaker-toronto-mk9k66spagk4) — Toronto, Canada
- [Paid Media Specialist](https://feeny.ai/job/paid-media-specialist-dealmaker-los-angeles-3pfewttqfrf6) — Los Angeles, CA
- [Financial Controller](https://feeny.ai/job/financial-controller-pylon-san-francisco-snfmn7m5fana) — San Francisco, CA
- [Financial Controller](https://feeny.ai/job/financial-controller-constantinople-sydney-5ztwtzqyeftw) — Sydney, Australia
- [Financial Controller](https://feeny.ai/job/financial-controller-43north-buffalo-33y51db84qxq) — Buffalo