Account Executive, Enterprise - Toronto - Nylas

Description

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 Team

The Enterprise Sales team at Nylas drives strategic growth by helping large organizations leverage our platform to modernize their communication and automation capabilities. We are a highly collaborative, performance-oriented group that partners closely with Customer Success, Product, and Engineering to deliver exceptional customer outcomes. Our team thrives on curiosity, creativity, and the pursuit of long‑term partnerships that create measurable business value.

The Role

We're expanding our Enterprise Sales team and are hiring two Account Executives with complementary areas of focus: Finance/Insurance and CRM applications.

In this role, you will focus on acquiring new enterprise customers and expanding existing strategic accounts. You bring a track record of selling complex SaaS solutions to large organizations, navigating multi‑stakeholder environments, and delivering seven‑figure outcomes.

As an Enterprise AE, you will own the entire sales process — from pipeline generation to negotiation and close — leveraging a consultative, solution‑oriented approach to help customers unlock the full potential of the Nylas platform. This is an exciting opportunity for an ambitious, customer‑focused sales professional who thrives in a dynamic, high‑growth environment.

What You'll Do

• Own and manage the full enterprise sales cycle, from prospecting and qualification through negotiation and close.

• Develop and execute strategic account plans to identify "land" opportunities and drive expansion across large organizations.

• Engage with senior stakeholders to understand business priorities and align Nylas's value to strategic outcomes.

• Lead discovery and solution‑selling conversations that uncover customer pain points, technical requirements, and desired business results.

• Partner with internal teams to deliver cohesive, high‑impact customer experiences.

• Manage complex deal cycles involving procurement, legal, and security reviews.

• Consistently achieve and exceed revenue targets while maintaining a healthy pipeline of qualified opportunities.

• Serve as a trusted advisor to customers, helping them leverage Nylas's APIs to accelerate digital transformation and automation initiatives.

• Provide market feedback and insights to influence product roadmap and go‑to‑market strategy for the enterprise segment.

What You'll Bring

• Experience: 5‑8 years of B2B SaaS sales experience, with at least 3+ years selling into enterprise accounts (Fortune 1000 or equivalent).

• Performance: Proven track record of exceeding annual quotas of $1M+ ARR, including closing large, multi‑year, or multi‑stakeholder deals.

• Enterprise Sales Expertise: Skilled in managing complex sales cycles (6–12+ months), navigating enterprise procurement and security processes, and executing "land and expand" strategies.

• Consultative Selling: Strong discovery, relationship‑building, and solution‑selling abilities — adept at crafting ROI‑driven business cases.

• Technical Acumen: Familiarity with modern APIs and SaaS infrastructure; able to effectively communicate technical concepts to both technical and non‑technical audiences.

• Collaboration: A team‑oriented mindset with experience working cross‑functionally to deliver customer success.

• Communication: Exceptional verbal and written communication skills with the ability to influence executive stakeholders.
  Drive: Highly motivated, organized, and adaptable; thrives in a fast‑paced startup environment and is passionate about driving impact through technology.
  

Interview Process

• Round 1: 30 minute Google Meet discussion with the Recruiter

• Round 2: 45 minute Google Meet discussion with the CEO

• Round 3: Take‑home assignment, followed by a 60 minute panel discussion

• Round 4: 2‑3 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.

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