Enterprise Account Executive

Greenspace Mental Health Ltd.; Toronto; Hybrid; CAD 420,000 - 480,000; Full time

Job summary

Greenspace Health is seeking an Enterprise Account Executive in Toronto for a hybrid role reporting to the VP of Sales. You will identify enterprise opportunities, manage a robust sales pipeline, and lead end-to-end cycles with large healthcare organizations.

Responsibilities include discovery, tailored demos, and multi-stakeholder negotiations. You will collaborate with marketing, product and customer success to refine messaging and drive growth, with a focus on value-based contracts and

Qualifications

• 5+ years of experience in an enterprise sales role, healthcare SaaS a plus.
• Ability to build and manage pipelines and identify decision-makers.
• Strong discovery, consulting and top-level stakeholder engagement.
• Post-secondary education; psychology/health background is a bonus.
• Excellent verbal and written communication; self-driven and results oriented.
• Hybrid work setup in Toronto, collaborating with cross-functional teams.

Responsibilities

• Own an enterprise territory and build an account plan for health systems and multi-site providers.
• Sell to the full buying committee, securing consensus across clinical, technical and financial stakeholders.
• Lead complex evaluations with tailored product demos and EHR integration scope.
• Develop pricing models and negotiate multi-year, multi-site contracts.
• Maintain accurate MEDDPICC-based forecasts and update Salesforce weekly.
• Iterate the enterprise sales playbook to improve outcomes.

Skills

Enterprise sales

Complex sales

Healthcare SaaS

Lead generation

Strategic thinking

Communication

Self-starter

Education

Post-secondary education

Bachelor's degree or equivalent

Tools

Salesforce CRM

Sales enablement tools

Job description

Company Description:

Greenspace Health is dedicated to ensuring that every person accessing mental health services should receive high quality care that helps them thrive. We work every day to empower mental health systems, providers and individuals in care with the MBC technology and data they need to continuously enhance care quality and drive measurable financial value for partner organizations.

Greenspace has worked with over 750 service delivery organizations across North America to implement Measurement-Based Care and enhance results for the people they serve. Greenspace is ranked as the #1 software for MBC & Outcomes Tracking by G2.

Role Description:

The Enterprise Account Executive is a full-time, hybrid role based in Toronto, ON, reporting to the VP of Sales. The individual will identify and pursue new enterprise opportunities, build and manage a robust sales pipeline, and lead end-to-end sales cycles with large healthcare and mental health organizations. Day-to-day responsibilities include generating and qualifying leads, conducting discovery meetings, delivering product demos tailored to stakeholder needs, and driving consultative sales conversations that highlight the value of Greenspace’s Measurement-Based Care solutions. The Enterprise Account Executive will negotiate contracts, collaborate with internal teams on proposals and implementation plans, and maintain long-term relationships to support client success and growth. The role requires close collaboration with marketing, product, and customer success teams to refine messaging, gather market feedback, and help shape Greenspace’s go-to-market strategy.

Specific Responsibilities:

• Own an enterprise territory. Build and execute an account plan for a defined set of health systems, large community behavioral health organizations and multi-site specialty providers. Prioritize based on fit, funding and timing.
• Sell to the whole buying committee. Run discovery and build consensus across clinical leadership (CMO, Chief Clinical Officer, VP Clinical Operations), technical and security stakeholders (CIO, CMIO, IT and InfoSec), finance (CFO, VP Finance), quality and compliance, and frontline program directors. Identify and develop an internal champion, and earn access to the economic buyer.
• Lead complex evaluations. Run tailored product demonstrations for mixed clinical and technical audiences, scope integrations with the customer's EHR. You will need to engage as a trusted consultant, developing mutual action plans by understanding an organization’s unique challenges and identifying opportunities to improve quality of care or align with their strategic priorities.
• Build and defend commercial structure. Construct multi-year, multi-site pricing; build the business case in the customer's terms (CCBHC and grant reporting requirements, value-based and payor contracting, quality metrics, clinician efficiency, outcome improvement); and negotiate to a signed agreement.
• Forecast with discipline. Qualify and maintain opportunities using MEDDPICC, keep Salesforce current, and deliver an accurate, defensible forecast in weekly pipeline reviews and monthly leadership updates.
• Iterate the enterprise playbook. Evaluate our sales process on an ongoing basis, and generate new strategies to improve outcomes.

Skills and Traits to be Successful:

• You are motivated by the Greenspace vision and align with our core values (www.greenspacehealth.ca/about-us).
• You have 5+years of experience in an enterprise sales role. Experience in a closing role, complex sales and Healthcare SaaS is valuable.
• You have demonstrated an ability to think strategically about sales and help define a successful process.
• You have completed post-secondary education (or have similar experience). A link to psychology/health is a bonus.
• You have very strong verbal and written communication skills.
• You are a motivated self-starter who hustles to guarantee success.

Diversity

We believe that diversity makes our organization stronger, and we are committed to being an equal opportunity employer. Greenspace recruits, employs, trains, compensates and promotes employees regardless of race, religion, colour, national origin, gender, age, sexual orientation, gender identity or disability.

Compensation

Your compensation package will be competitive and involve (i) base salary, (ii) commission on sales and (iii) equity (stock options) in a fast-growing company. OTE for this role is $320,000.00.

Qualifications

• Demonstrated experience in Software Sales and enterprise Sales, preferably in healthcare, healthtech, or SaaS environments.
• Proven ability in Lead Generation and prospecting, including building and managing pipelines and identifying key decision-makers.
• Comfort with travel as needed and presentations to large groups of stakeholders.
• Expertise in Consultative Selling, including conducting discovery, understanding client workflows, and tailoring solutions to complex organizational needs.
• Excellent communication, presentation, and negotiation skills, with comfort engaging executive-level stakeholders.
• Ability to work effectively in a hybrid environment in Toronto, ON, collaborating in person and remotely with cross-functional teams.
• Goal-oriented mindset with a track record of meeting or exceeding sales targets and using data to inform sales strategies.
• Experience with CRM tools (e.g., Salesforce or similar) and sales enablement platforms.
• Understanding of mental health, healthcare delivery, or outcomes measurement is an asset.
• Bachelor’s degree in Business, Marketing, Health Administration, or a related field, or equivalent professional experience.