Director of Sales, Nylas
Enterprise
CA$290-390k
+ Commission Plan + Equity Package
Expert level
Remote from Canada
More information about location
Productivity APIs for work automation
Be an early applicant
Productivity APIs for work automation
101-200 employees
B2BArtificial IntelligenceSecurityProductivityCommunicationSaaSAPIAutomation
Be an early applicant
CA$290-390k
+ Commission Plan + Equity Package
Expert level
Remote from Canada
More information about location
101-200 employees
B2BArtificial IntelligenceSecurityProductivityCommunicationSaaSAPIAutomation
Company mission
To help developers leverage communications data and build features that increase customer engagement, productivity, and retention.
Role
Who you are
- 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)
What the job involves
- 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!
- 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
Application process
- 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)
Our take
Nylas provides productivity infrastructure solutions for modern software. Over 200,000+ developers use their powerful suite of tools to quickly and securely build productivity features into their applications, resulting in 12 billion+ API requests per day.
The number of businesses using their platform is rapidly increasing due to the Nylas infrastructure generating huge operational savings through more productive, secure, and intelligently-automated development cycles.
The company has remained focused on scaling its integrated and productivity-driven developer experience as well as furthering its investment in disruptive technologies that automate workflows and seamlessly integrate technologies such as conversational AI, Natural Language Processing (NLP), Optical Character Recognition (OCR), and cross-system intelligent automation.
Steph
Company Specialist at Welcome to the Jungle
Insights
Led by a woman
Top investors
89% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Jun 2021
$120m
SERIES C
Jun 2020
$25m
SERIES B
Total funding: $173m
Company 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
Company HQ
Tenderloin, San Francisco, CA
Leadership
Christine Spang
(Board Member & CTO)Previously worked as Principal Developer at Oracle for 1 year and as Laboratory Assistant at MIT for 1 month.
Gleb Polyakov
(CEO)Previously Operations Consultant at B&G International for 1 year and Crowdfunding Director at Parallax Creative for 3 years.
Share this job
View 1 more job at Nylas