Enterprise SaaS Sales Leader

Hybrid or Remote (Secure Engage – Canada/US) Type: Full Time Key Responsibilities Own the full sales cycle for enterprise clients across Canada—prospecting, pitching, negotiating, and closing. Build relationships with compliance, legal, procurement, and risk teams within financial institutions and regulated sectors. Understand client pain points around third‑party risk, regulatory pressures, and cybersecurity—and translate these into tailored solutions using Secure Engage’s platform. Drive platform adoption and expand client accounts through cross‑sell and upsell opportunities. Maintain accurate pipeline tracking and forecasting in CRM. Partner with product and customer success teams to ensure client satisfaction and identify opportunities for product feedback. Required Skills & Qualifications 5+ years of experience in enterprise B2B SaaS sales, ideally in compliance, security, or legaltech. Demonstrated ability to sell into complex enterprise environments, including banks, insurers, and large law firms. Deep understanding of sales processes, pipeline management, and value‑based selling. Strong presentation, negotiation, and relationship‑building skills. Experience navigating Canadian regulatory environments is a plus. Self‑starter with startup grit—able to thrive in a high‑growth, dynamic environment. What We Offer Remote‑first with flexibility to meet enterprise clients in person across Canada. Competitive base salary, commission, and equity options. Paid time off and flexible scheduling. Opportunity to help shape the future of cybersecurity compliance. Collaborative team culture with real impact on product and strategy. Head of Compliance and Regulatory Affairs Hybrid or Remote (Secure Engage – Canada/US) Lead the development and execution of Secure Engage’s compliance strategy across North American and international regulatory frameworks (OSFI B‑10, DORA, OCC, etc.). Collaborate with product, engineering, and legal teams to ensure platform readiness and defensibility against financial regulatory standards. Own and execute the overall sales and go‑to‑market strategy for Secure Engage across North America. Build and lead a high‑performance sales team focused on enterprise clients (banks, insurers, law firms, regulators). Lead the post‑sale customer journey—from onboarding to renewal—ensuring enterprise clients receive measurable value from the Secure Engage platform. Build and maintain strong relationships with compliance, legal, and procurement stakeholders at financial institutions and their HRHT third parties. Lead Secure Engage’s fundraising strategy, including preparation of investor materials, pitch support, and financial due diligence. Manage the end‑to‑end fundraising process—from pipeline development to deal structuring and closing. Own and lead Secure Engage’s global marketing strategy, with a focus on demand generation, brand awareness, and thought leadership in the compliance, legaltech, and cybersecurity space. Build a strong digital and content marketing engine, with clear messaging tailored to CCOs, CISOs, GCs, and regulatory stakeholders in financial institutions and HRHT sectors. Act as the technical bridge between Sales, Product, and prospective clients—translating complex platform capabilities into clear, compelling value propositions. Support the sales team during discovery, demos, and technical evaluations with banks, insurers, and law firms. Full Stack Software Developer (Ruby on Rails, React, Python) Hybrid or Remote (Secure Engage – Canada/US) Secure Engage is redefining how organizations manage cyber and regulatory risk using AI. We’re looking for a Full Stack Software Developer to help us build and scale our platform—from back‑end infrastructure to front‑end user experiences. Accountant Hybrid or Remote (Secure Engage – Canada/US) Secure Engage is a fast‑growing SaaS company focused on AI‑powered cybersecurity and compliance. We’re looking for a detail‑oriented, proactive Accountant to manage day‑to‑day financial operations, assist with month‑end reporting, and ensure our books are accurate and audit‑ready. COO Hybrid or Remote (Secure Engage – Canada/US) Secure Engage is a fast‑growing, AI‑powered platform transforming how organizations manage cybersecurity and compliance across high‑risk, high‑trust (HRHT) relationships. As we scale, we’re looking for a strategic and execution‑focused COO to lead day‑to‑day operations and help drive growth across product, customer success, and revenue teams. #J-18808-Ljbffr