Sales Manager (Individual Contributor)

DealMaker; Toronto; On-site; CAD 50,000 - 120,000; Full time

Job summary

Join an innovative fintech company that is transforming the capital markets ecosystem. As a sales professional, you will leverage your expertise to close deals with medium to large clients, utilizing strategic prospecting and relationship-driven sales techniques. This role offers the chance to work in a fast-paced environment where your contributions will directly impact the company's growth. With competitive compensation, equity opportunities, and a supportive team, this is an exciting opportunity to be part of a dynamic startup on the rise.

Benefits

Competitive compensation

Equity opportunities

Shared employee benefit plan

Annual learning support

Strong autonomy with support from leadership

Qualifications

• 4-5 years of experience in sales, ideally in fintech or capital markets.
• Proven success in closing mid-market to enterprise-level deals.

Responsibilities

• Create and close new business opportunities with large customers.
• Manage a pipeline of qualified prospects through various channels.
• Drive full-cycle sales motions from prospecting to closing.

Skills

Strategic prospecting

Solution selling

CRM skills (HubSpot/Salesforce)

Communication skills

Relationship-driven sales

AI-driven sales tools

Education

Bachelor's degree in Business or related field

Tools

HubSpot

Salesforce

Clay

Apollo

LinkedIn Sales Navigator

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’re a proven sales professional with 4–5 years of experience closing deals in a fast-paced environment. Ideally, you bring a background in fundraising, equity crowdfunding, private capital markets, or financial technology. You're self-motivated, outcome-obsessed, and comfortable operating independently to deliver results. You excel at creating and closing new opportunities while building strong, long-term customer relationships that drive repeat and referral business. You are a relationship-driven seller who can build trust quickly, cultivate referral partners, and navigate mid-market to enterprise deal cycles with confidence. You know how to prioritize speed over perfection, drive outcomes, and push your limits to find a way forward for your customers

What you will do

-Create and close new business opportunities with Medium, Large, and Extra-Large customers.

-Build and manage a pipeline of qualified prospects through a mix of outbound, inbound, referrals, and partnerships.

-Drive full-cycle sales motions: prospecting, solution positioning, negotiation, and close.

-Cultivate deep relationships with customers to maximize expansion, referrals, and long-term loyalty.

-Manage and leverage a dedicated BDR resource to help create qualified pipeline and accelerate opportunity creation.

-Develop and grow relationships with key referral partners to expand market reach.

-Collaborate with internal teams to innovate, simplify, and improve sales processes.

-Operate in a metrics-driven environment focused on closed-won setup revenue.

-Utilize AI tools and data insights to enhance prospecting, outreach, and deal management efficiency.

What skills you need

-Strategic prospecting and territory development, including account mapping and multi-threading.

-Proven success closing mid-market to enterprise-level deals ($50K–$500K+).

-Ability to manage and coach a BDR to drive pipeline generation in alignment with personal sales goals.

-Expertise in solution selling, challenger sales, and relationship-driven sales methodologies.

-Strong CRM skills (preferably HubSpot or Salesforce) for pipeline management and forecasting.

-Familiarity with AI-driven sales tools (ex: Clay, Apollo, LinkedIn Sales Navigator) to boost efficiency and effectiveness.

-Sharp communication—bold, direct, clear, and highly customer-centric.

-Resourcefulness, creativity, and resilience to "find a way" in complex and competitive sales environments.

-Ability to thrive in a fast-moving, outcome-focused culture that prioritizes speed, innovation, and customer obsession.

Founded in 2018 by leading capital markets lawyers, DealMaker has blazed its own trail as the leading online capital-raising platform. As a Series 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)

-Strong autonomy with support from leadership

-Annual learning support And more!

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.