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 Director of Sales, Enterprise to spearhead our enterprise go-to-market strategy and build out our enterprise sales function. Reporting directly to the CEO, this leader will own and drive Nylas’s enterprise sales motion, working closely with the CEO and CFO to align on strategy and revenue goals. You will manage a team of 6–8 enterprise-focused team members (Account Executives, Solutions Engineer(s), and other GTM staff) and be responsible for scaling a high-performance team and repeatable sales process in the enterprise segment. This is a highly strategic and hands-on role for a proven sales leader who can shape our enterprise GTM strategy, coach and develop talent, and lead by example in engaging with our most strategic customers. If you are excited to build an enterprise sales engine from the ground up in a developer-focused platform company, we’d love to talk to you!

What You’ll Do

• Enterprise Sales Strategy: Develop and execute Nylas’s enterprise sales strategy (in collaboration with the CEO and CFO) to drive new business and expansion in our target markets. Define territory coverage, target verticals/use cases, and a clear plan to meet and exceed enterprise revenue goals.
• Team Leadership: Lead, manage, and mentor a team of ~6–8 Enterprise Account Executives, Sales Engineers, and other GTM staff. Foster a high-performance, accountable sales culture that consistently hits targets. Attract and retain top sales talent, and build a culture of coaching, excellence, and “inspect what you expect” accountability.
• Revenue Ownership: Drive consistent attainment of enterprise sales targets (new ARR and expansion bookings), while maintaining disciplined pipeline management, forecast accuracy, and deal execution rigor. Implement an operating cadence of pipeline reviews and sales forecasting to ensure predictability and transparency.
• Sales Process & Playbook: Establish and continually refine a scalable enterprise sales playbook and process. This includes defining sales stages, qualification criteria, and best practices for complex, multi-stakeholder sales (from initial prospecting through negotiation and close). Ensure the team leverages modern sales methodologies (MEDDIC, Challenger, etc.) and a data-driven approach to optimize win rates.
• Deal Leadership (Player/Coach): Provide executive sponsorship and leadership on strategic deals while also taking the field when needed. Coach the team through complex 6– and 7–figure sales cycles—joining customer calls, running executive pitches/whiteboards, removing obstacles, and guiding negotiations to close high-value, multi-year contracts. Directly contribute to the creation and customization of strategic sales materials (C-suite decks, ROI/TCO models, proposals/SOWs, mutual action plans) to elevate win probability. Help navigate enterprise procurement, security reviews, and legal processes, and build relationships with C-level stakeholders (CIO, CTO, VP Engineering, etc.) to win their trust.
• Hands-On Sales Materials & Enablement (Player/Coach): Personally develop and refine enterprise collateral and talk tracks—ICP/vertical decks, discovery frameworks, MEDDICC artifacts, business cases, competitive one-pagers, case studies—and partner with SE/Marketing to productize them into a maintained content library. Jump in as an IC for top-priority pursuits (prospecting into target accounts, leading discovery, shaping POCs/Pilots, and building mutual success plans), while capturing win/loss insights to continuously improve the playbook.
• Cross-Functional Collaboration: Work tightly with cross-functional teams to accelerate enterprise deals and ensure customer success. Partner with Marketing on account-based campaigns and pipeline generation, with Product on aligning roadmap/value props to enterprise needs, and with Customer Success/Support to guarantee smooth onboarding and long-term value for enterprise customers. Coordinate with Solutions Engineering on technical win strategies and with Finance (CFO) on deal economics and forecasting.
• GTM Execution & Enablement: Translate high-level company goals into executable go-to-market plans for the enterprise segment. Set quarterly and annual enterprise sales targets, and work with Revenue Operations (if available) to implement dashboards and metrics for pipeline health, sales cycle, and conversion rates. Drive initiatives to generate enterprise pipeline (outbound efforts, strategic partnerships, AWS marketplace or channel opportunities, etc.) and ensure the team is enabled with the right tools, product knowledge, and training to succeed.
• Customer Advocacy & Market Presence: Act as a senior ambassador of Nylas in the enterprise market. Develop executive-level relationships with key clients, ensuring their feedback informs our strategy. Represent Nylas at industry events and in front of enterprise prospects, evangelizing our API-first platform vision and delivering a compelling ROI-focused message.

(Note: This role may carry a limited personal sales quota or strategic account ownership, but the primary focus is on leading and scaling the team to achieve collective goals.) What You’ll Bring

• Experience: 10+ years of success in B2B SaaS/tech sales, with at least 3–5 years in a sales leadership role (enterprise focus preferred). A track record of exceeding revenue targets and scaling out new sales teams or territories in a high-growth environment is essential.
• Domain Knowledge: Expertise in selling technical products – ideally developer tools, APIs, or infrastructure software – to technical and business stakeholders. Experience selling to developers, Product/Engineering leaders, or IT/infrastructure buyers is a strong plus (you understand how to articulate value through security, reliability, and productivity drivers).
• Enterprise Sales Acumen: Proven ability to close complex, high-value deals with Fortune 1000-level enterprises. Comfortable navigating multi-stakeholder sales cycles, including engaging C-suite executives and handling complex procurement and compliance processes. You are an enterprise seller at heart, adept at consultative and value-based selling at the executive level.
• Leadership & Coaching: Exceptional team leadership skills with experience hiring and developing top-performing salespeople. You are a hands-on coach who can motivate a team, provide constructive feedback, and uplevel the skills of those around you. You’ve built a positive, inclusive sales culture that balances accountability with celebration.
• Strategic & Analytical Mindset: Strategic thinker who can craft a go-to-market strategy and also dive into the details of execution. Data-driven and analytical; you use metrics to inform decisions and can implement process improvements to drive efficiency and predictability in the sales org. Familiarity with modern sales methodologies and operating cadences (e.g. MEDDICC, Challenger Sale, weekly forecast reviews) to manage pipeline and forecast with accuracy.
• Communication & Influence: Excellent communication, presentation, and negotiation skills. Able to communicate a crisp value proposition and ROI story to enterprise executives. You have strong executive presence – comfortable leading boardroom-level discussions as well as internal strategy meetings. High emotional intelligence with the ability to influence and build trust across both customer organizations and internal teams.
• Cross-Functional Collaboration: Demonstrated success working cross-functionally to drive outcomes. You appreciate the value of aligning Sales with Marketing, Product, Finance, and Customer Success, and have experience being the “voice of the customer” internally to shape product and strategy.
• Entrepreneurial Drive: Thrives in a fast-paced, scaling startup environment. You take ownership, move with urgency, and adapt quickly to new learnings or market feedback. A proactive, action-oriented operator who leads from the front – you don’t hesitate to roll up your sleeves alongside your team to win business.
• Education: Bachelor’s degree or equivalent experience required. MBA or advanced education is a plus but not required.
• Travel: Willingness to travel as needed (estimated 20%) to meet with strategic customers and attend key industry events (this is a customer-facing leadership role)

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 $290,000 - $390,000 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.