AI GTM Specialist at DealMaker in Toronto

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’re early in your sales or growth career and ready to learn fast, push hard, and grow into a world-class revenue professional. You aren’t just a traditional seller; you are a builder. You are energized by the idea of helping innovative companies raise capital online, and you are fascinated by how AI and automation can supercharge the sales process to do it efficiently.

You thrive in a fast-moving environment where speed matters more than perfection. You love tinkering with data, building automated workflows, and testing new approaches to reach the right person at the right time. You’re curious, coachable, and relentless when it comes to finding a way forward. Above all, you’re driven by impact: helping real businesses succeed through smarter fundraising.

What you will do

As a AI GTM Specialist you’ll be responsible for creating qualified pipelines with high-value buyers in our Ideal Customer Profile (ICP). You’ll partner closely with a senior Account Executive to run coordinated outbound plays, but you will act as the technical engine of the outreach—leveraging AI and automation to engage executives at scale and identify real deal opportunities.

This role is a springboard to a high-level career in tech sales and revenue operations. You’ll develop your outbound prospecting skills, master cutting-edge sales technology, and learn the fundamentals of capital markets—all while being mentored by some of the best in the business.

The most critical part of this role is partnering with a senior seller to create a qualified, high-quality pipeline through scaled, intelligent outreach. You will:

• Automate List Building: Use modern tools to quickly find, organize, and enrich lists of target accounts across our key industries.

• Scale Outreach with AI: Leverage AI tools to craft, test, and execute highly personalized, multi-channel outbound campaigns (email, phone, LinkedIn, etc.) at scale.

• A/B Test & Optimize: Continuously analyze open rates, reply rates, and conversion metrics to refine your AI prompts, messaging, and automation sequences.

• Drive Revenue: Book and qualify meetings with executive-level decision-makers.

• Strategize with AEs: Partner with Account Executives to build account strategies and deploy targeted plays based on the data and signals you uncover.

• Maintain CRM Hygiene: Track activity, automation workflows, and insights accurately in HubSpot CRM.

• Hit Quota: Consistently hit monthly targets for meetings booked and pipeline generated.

• Master the Market: Stay sharp on DealMaker’s value prop and market trends.

What skills you need

• Prior BDR, SDR, or Growth Operations experience in a SaaS or fintech company.

• Demonstrated experience using AI tools to enhance productivity, craft messaging, or optimize sales processes.

• Familiarity with automation, data enrichment, and list-building tools (e.g., Clay, Apollo.io, Zapier, Phantombuster, or similar).

• An analytical mindset with the ability to troubleshoot, iterate, and optimize outreach workflows based on data.

• Hunger to learn and grow in tech sales.

• Comfort with rejection and a drive to outperform expectations.

• Strong written and verbal communication skills.

• Attention to detail and ownership over your outreach architecture.

• Curiosity, coachability, and a bias toward action.

• Familiarity with HubSpot, LinkedIn Sales Navigator, or other core outbound tools.

• Interest in capital markets, crowdfunding, or venture funding.

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.