AI GTM Specialist

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 oursand our track record speaks for itself with over $2B raised across 1000 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.

Youre early in your sales or growth career and ready to learn fast push hard and grow into a world-class revenue professional. You arent 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. Youre curious coachable and relentless when it comes to finding a way forward. Above all youre driven by impact: helping real businesses succeed through smarter fundraising.

As a AI GTM Specialist youll be responsible for creating qualified pipelines with high-value buyers in our Ideal Customer Profile (ICP). Youll partner closely with a senior Account Executive to run coordinated outbound plays but you will act as the technical engine of the outreachleveraging 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. Youll develop your outbound prospecting skills master cutting-edge sales technology and learn the fundamentals of capital marketsall 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 DealMakers value prop and market trends.

• 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 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 a tech startup we are well-capitalized firmly established in our market and ready to scale. Heres why you should want to join us:

• Competitive compensation with the opportunity to earn equityget 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 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 individuals 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.

Required Experience:

IC