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Enterprise Account Executive

Nylas5 days ago
Remote
Canada
CA$99,680 - CA$135,279/yearly
Senior Level

Top Benefits

Retirement plans
Wellness stipend
12 weeks paid parental leave

About the role

Who you are

  • You bring a track record of selling complex SaaS solutions to large organizations, navigating multi-stakeholder environments, and delivering seven-figure outcomes
  • This is an exciting opportunity for an ambitious, customer-focused sales professional who thrives in a dynamic, high-growth environment
  • 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

What the job involves

  • 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
  • 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
  • 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
  • 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

The application 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

Benefits

  • Retirement plans
  • Wellness stipend
  • Paid parental leave: 12 weeks parental leave (maternity & paternity)
  • Annual learning & development perk
  • Voting/Election PTO: 4 hours of paid time off to vote in person or volunteer at a polling place
  • Unlimited paid time off policy
  • Work from home opportunities
  • Health insurance

About Nylas

Software Development
201-500

Hundreds of thousands of developers around the world use Nylas to increase velocity and seamlessly build customizable email and scheduling capabilities through state-of-the-art APIs. Nylas is the only platform giving developers universal access to email, calendar, and contacts providers through a single integration.