The Company At Nylas, we specialize in making it easier for developers to add email, calendar, and contact management features into their applications. We provide APIs, which streamline the integration of these functionalities, ensuring they are secure and effective. This enables better, safer, and more reliable communication within apps.

Supporting over 100,000 developers and collaborating with more than 900 companies globally, Nylas plays a pivotal role in how digital communication tools are built and utilized. Our technology spans various sectors, from healthcare to education, simplifying the complex process of app development related to communications. By reducing the barriers in communication technology, we empower developers to innovate and enhance user interaction across platforms.

The Role We are seeking a Lead Account Executive, Enterprise to spearhead our enterprise sales efforts. In this role, you will serve as the primary enterprise sales leader on our team, owning a portfolio of high-value accounts and opportunities. You will leverage your 10+ years of SaaS enterprise sales experience to navigate complex, multi-stakeholder deals and long sales cycles, engaging C-level executives and championing Nylas’s value at every step. This is a high-impact, senior individual contributor position – you will develop and execute account strategies, employ a consultative solution-selling approach, and act as a trusted advisor to our most strategic clients. If you are a driven sales professional who excels at landing new enterprise wins, all while collaborating cross-functionally in a fast-paced startup environment, we’d love to hear from you.

What You’ll Do

• Strategic Account Development: Develop and execute comprehensive account plans for a targeted portfolio of enterprise customers. Identify key initial “land” opportunities. Cultivate multi-threaded relationships that lead to broad adoption of Nylas across the enterprise.
• Full-Cycle Enterprise Selling: Own and manage the entire sales cycle for complex deals, from initial prospecting and discovery through solution presentation, negotiation, and close. Drive disciplined opportunity management – qualifying, forecasting, and closing large contracts – while maintaining a robust pipeline of new business. Consistently meet and exceed quarterly and annual revenue targets.
• Executive Engagement: Build and nurture trusted advisor relationships with senior client stakeholders, including VP and C-suite executives. Lead executive-level discussions to understand strategic objectives and align Nylas’s solutions to business outcomes. Navigate enterprise procurement processes and proactively address executive concerns to secure buy-in and long-term commitment.
• Consultative Solution Selling: Take a consultative, value-driven approach to sales. Deeply understand each customer’s technical requirements and business challenges in order to craft tailored solutions that demonstrate clear ROI. Educate clients on industry best practices and position Nylas’s platform as a critical component of their digital transformation and workflow automation strategies.
• Cross-Functional Collaboration: Orchestrate and leverage cross-functional teams to win and grow enterprise accounts. Work closely with Solutions Engineering on technical proofs-of-concept, Customer Success and Support to ensure successful onboarding, and Product and Marketing to address enterprise requirements. By coordinating these resources, deliver a cohesive and exceptional customer experience at scale.
• Market Leadership: Stay informed on industry trends, competition, and the evolving needs of enterprise developers and IT teams. Advocate for your customers by bringing insightful feedback to Nylas’s leadership and product team, helping to shape our roadmap and go-to-market strategy for the enterprise segment. Act as an internal leader for enterprise sales best practices, mentoring junior team members and contributing to a culture of excellence and continuous improvement.

What You’ll Bring

• Experience: 10+ years of B2B SaaS sales experience, with at least several years dedicated to selling into large enterprise accounts (Fortune 1000 or equivalent). A proven track record of successfully closing new business and expanding existing accounts at the enterprise level is required.
• Performance: Demonstrated ability to consistently meet and exceed ambitious sales targets. You have a history of overachievement against annual quotas on the order of $1M+ ARR (or higher), including winning seven-figure deals and managing multi-year contracts.
• Enterprise Sales Expertise: Extensive experience managing long, complex sales cycles (often 6-12+ months) with multiple stakeholders. Skilled at navigating enterprise procurement, legal, and security review processes. Adept at “land and expand” strategies – you know how to win initial projects and then grow them into larger deployments over time.
• Strategic & Consultative Skills: Strong strategic account planning and consultative selling abilities. You can develop long-term enterprise account plans, identify upsell/cross-sell opportunities, and become a trusted advisor to your clients’ senior leadership. Excellent discovery, listening, and problem-solving skills with a solution-oriented mindset.
• Cross-Functional Leadership: Proven ability to collaborate and influence in a cross-functional environment. You work well with sales engineers, product managers, customer success and others to galvanize support for your deals and ensure customer success. (Experience leading internal pursuit teams or a “pod” selling approach is a plus.)
• Technical Acumen: Familiarity with modern cloud software and APIs; ability to quickly learn the ins and outs of Nylas’s developer platform. You are comfortable engaging with technical audiences (developers, CTOs) and can effectively communicate technical solutions to non-technical stakeholders. An aptitude for learning new technical concepts is essential (a background in computer science or engineering is a bonus).
• Communication & Influence: Exceptional communication and interpersonal skills. Able to craft and deliver compelling presentations and product demos to audiences ranging from engineers to C-level executives. Strong negotiation skills with experience navigating enterprise contract discussions to favorable outcomes.
• Drive & Work Ethic: Self-motivated, entrepreneurial mindset with a high degree of ownership and accountability. Thrives in a fast-paced, growing startup environment. You demonstrate a growth mindset, resilience, and a passion for helping customers succeed. You continually seek to improve your craft and share knowledge with the team.

Interview Process (subject to change)

• Round 1: 60 minute Google Meet discussion with the CEO
• Round 2: 60 minute Google Meet discussion with the CFO
• Round 3: Three (3) Google Meet discussions with various Nylas members (max 3 hours).

Throughout the interview process, we encourage you to discuss concrete examples of your past enterprise sales achievements – be ready to walk us through the what, why, and how of significant deals you’ve led. We want to understand your strategy, thought process, and how you execute on complex opportunities.

The estimated total on-target earnings (OTE) range for this position is $200,000 - $275,000 CAD. Actual compensation will be determined based on individual qualifications and performance during the hiring process. Factors influencing the offer include your depth of experience, proven skills, and track record of results in enterprise sales. Nylas also offers a competitive commission plan and equity package aligned with our stage and growth trajectory.

Nylas is registered as an employer in many, but not all, states/provinces. If you are not located in or able to work from a state/province where Nylas is registered, you will not be eligible for employment. Visa sponsorship may not be available in certain remote locations.