Founding Account Executive

Company Overview Datascout Datascout is a Bursting Silver company, part of the world's largest implementer of iMIS. We help unions, regulatory bodies, and industry associations modernize how they communicate and engage with their members - using AI-powered email and engagement tools that are built for organizations where trust, privacy, and institutional credibility are non-negotiable. Our platform integrates with the systems nonprofits already rely on - CRMs, AMS platforms, custom databases, and modern cloud tools - so organizations don't need to rebuild their tech stack to benefit from AI. Bursting Silver Bursting Silver is a purpose driven, professional services technology consulting company. A 2-time Top 100 Best Workplaces in Canada and 4-time Great Place to Work® Certified company, we're focused on delivering technical solutions to Canadian and US non-profit’s, including professional associations, unions, regulatory bodies and non-governmental agencies. Our service offerings include A.I. products, like Datascout, mobile applications, web-based applications, IT strategy, business analysis, project management, data migrations, system upgrades and application support. Role Overview We are seeking a Founding Account Executive to join our Datascout product team on a permanent, full-time basis. As one of our first Account Executives, you're not walking into a finished sales engine. Few warm leads are waiting for you, and there are no SDR's handing you qualified meetings. What there is: a committed team, a genuinely differentiated product, a market that needs what we've built but doesn't know it yet, and real commercial opportunity for someone willing to do the work of educating a skeptical audience. The organizations you'll be speaking with - unions, associations, regulatory bodies - move deliberately. They're cautious about AI for reasons that are legitimate. Cost perception, data privacy, and past experiences with over-promised technology are real objections, not noise. Your job is to meet those concerns head-on, with honesty and patience, and convert long-cycle relationships into genuine partnerships. If you're looking for a role where you can close a deal in two calls, this isn't it. If you're energized by the idea of winning the trust of an audience that doesn't trust easily - and building something that lasts - keep reading. Who we are looking for: You are an ambitious and accountable person, who is driven by serving clients, has a passion for technology, and loves to find creative solutions to solve tough problems You are smart, agile, and self-motivated and can take an assignment head-on and run with it You are strategy focused - You take a logical, analytical approach to your work and can see the bigger picture You are a strong communicator (English) with a friendly and helpful personality You have a disciplined 'get it done' work ethic that will allow you to work productively in a variety of environments – whether at the office, a client’s office, at your home office…or even on the go You are all about Team - Although we may not always be at the same place or working on the same project – we are always connected and communicating with one another to support each other. We leverage technology to the max You care. About your clients, your team, and your community. Giving back is such an integral part of what we do You are eligible to work full-time, unrestricted in Canada or the United States Key Responsibilities The successful candidate will be responsible for a range of duties and tasks including, but not limited to, the following: Build pipeline from the ground up: Develop new business opportunities across target verticals - unions, regulatory bodies, and industry associations - using a creative, multi-channel prospecting approach that goes beyond standard outreach. This includes research-led personalization, referral development, participation in industry forums and events, and digital prospecting. You are the source of your own pipeline. Lead the full sales cycle with discipline: Own every stage from prospecting through close: qualification, discovery, proposal, negotiation, and contract execution. Maintain rigorous CRM hygiene throughout - every touchpoint logged, every next step documented, every forecast delivered with accuracy and intention. Run consultative discovery that connects to real problems: Facilitate conversations that surface the genuine communication and member engagement challenges your prospects are facing, then connect those challenges to specific capabilities of the platform - in a way that feels relevant and credible to that particular organization, not templated. Educate prospects and address AI misinformation directly: Many of your conversations will require active myth-busting before any sales motion is possible. Be the resource your prospects need to understand what AI can and cannot do, how their member data is protected, and why the concerns they've heard aren't necessarily applicable here. This isn't a soft skill - it's a core part of the commercial role. Manage multi-stakeholder relationships across the full cycle: These sales don't run through one person. Build and sustain relationships across executive leadership, communications and operations teams, IT, and legal or compliance contacts - keeping each informed, engaged, and moving toward a decision without losing any of them along the way. Handle objections with confidence: Cost consciousness, data privacy concerns, and potentially resistance to change are the standing objections in this market. You address them directly, with evidence and empathy, and you know the difference between a delay and a dead deal. Feed intelligence back into the organization: As one of the first people selling this product in these markets, your field observations are genuinely valuable. Share what you're hearing - objections, competitor mentions, messaging that lands, positioning that doesn't - so leadership and the broader team can refine the go-to-market approach in real time. Represent the brand where your buyers gather: Attend and actively participate in industry events, association conferences, and membership forums. Not just to collect business cards - to establish presence, build credibility over time, and create the kind of visibility that shortens future sales cycles. A note on what this role is not This isn't the right fit if you're looking for an inbound lead queue, or a 30-day sales cycle. If the idea of a 6-month relationship-building process before a signature sounds exhausting, this probably isn't the right stage for you. But if that process sounds like the most interesting part of the job, you may be exactly who we're looking for. Role Requirements 5-7 years of B2B Sales experience in a A.I./Technology Product or SaaS sales environment, ideally in the technology and/or consulting industries. Experience in consultative, complex, or long-cycle roles - the kind where relationships and credibility matter as much as product features. A verifiable track record of quota attainment, ideally in environments where you were building pipeline from scratch rather than working a developed territory. Direct experience managing sales cycles of 3 - 6 months or longer, involving multiple decision-makers across different functions (executive, communications, IT, legal, or compliance). Strong CRM discipline - you treat your pipeline as a strategic asset and your forecasting as a commitment, not a guess. Demonstrated ability to handle complex objections - particularly around cost, data privacy, and technology skepticism - without deflecting, over-promising, or caving on value. Working familiarity with AI or SaaS solutions - enough to speak accurately about capabilities, address misinformation confidently, and discuss data handling in plain language. Proven comfort in early-stage or startup environments, where resources are lean, processes are still forming, and ambiguity is the norm rather than the exception. Strong communication skills across written, verbal, and presentation formats - you can adjust your register from a one-on-one with an IT director to a formal presentation to an association board. Desired Attributes Consultative and education led: You don't lead with a demo. You lead with questions, and you earn the right to propose solutions by understanding the problem first. In markets where the audience can be skeptical of technology, your approach is the differentiator. A self-starter with real discipline: You don't need someone to hand you a list of contacts or a script. You build your own pipeline, set your own cadence, and hold yourself accountable to the activity that drives results -even when no one's watching. Creative in how you prospect: Cold email alone won't crack these markets. You think strategically about where your buyers gather, what earns credibility in their world, and how to show up as someone worth listening to - not just another vendor. Thick-skinned but empathetic: Multi-touch point sales cycles and long silences before a signed contract come with this territory. You don't spiral when a decision takes longer than expected — you stay present, stay useful, and know when to push and when to wait. Trustworthy, not just persuasive: . In institutional markets, your personal credibility often precedes the company's brand. You understand that, and you protect it in every interaction. Comfortable building without a net: You're energized by the early-stage challenge - contributing to playbook development, refining messaging based on what you're hearing in the field, and helping shape a commercial function, not just executing inside one. Knowledgeable about AI without being evangelical: You can talk about what AI does and doesn't do with honesty and specificity. You know how to address data privacy concerns without being dismissive, and you don't oversell the technology. Preferred but not required: Experience selling into membership-based organizations, associations, unions, or regulated industries What We Offer Excellent pay & comprehensive benefits package. 2-time Top 100 Best Workplaces in Canada & 4-time Great Place to Work® Certified company. 4-day work week during the summer months & flexible work hours around our core hours. “Remote First” environment with flexible work & office locations. Regular company social events, games nights, virtual and in-person. Annual fully paid company retreat. Considerable paid time off including vacation days, wellness days, and additional leave options. A tight-knit, committed and knowledgable team Genuine opportunities for growth and development within the company. If you are interested in hearing more about this position or to apply, please submit your application via our application portal today!