Director, Enterprise Sales

Cliniconex; Ottawa; Hybrid; CAD 125,000 - 135,000; Full time

Benefits offered by this job

Flexible Hybrid Work Model

30 Days of Paid Time Off

Health & Wellness Budget

Internet Budget

Make a Real Impact

Collaborative Culture

Growth & Development

Day-One Benefits & Flexibility

Job summary

Cliniconex is seeking a Director of Enterprise Sales to lead growth in mid-market and enterprise segments from Kanata in a flexible hybrid setup. You will oversee two Enterprise Sales Account Managers, one SMB Account Manager, and a contract SDR team, driving strategy, forecasting, and collaboration across Marketing and Product.

You'll report to the Chief Revenue Officer and shape programs to scale revenues toward a $50M+ trajectory while ensuring deal closure, pricing, and procurement reviews

Qualifications

• 7+ years of sales leadership experience, preferably in mid-market or enterprise B2B software sales.
• Proven track record of moving an organization upmarket from SMB to mid-market and enterprise segments.
• Experience scaling revenue toward multi-million dollar businesses and building scalable processes.

Responsibilities

• Own the enterprise sales cycle end to end with forecast discipline.
• Identify and lead RFP, RFI, RFQ opportunities with cross-functional alignment.
• Direct the SDR team on outbound targeting and meeting quality for mid-market and enterprise accounts.
• Collaborate with Marketing, Customer Success and Product to improve lead generation and conversion.
• Serve as the closer for high-value deals, including pricing and contract negotiation.
• Provide insights to the Chief Revenue Officer on market trends and performance.

Skills

Sales leadership

Enterprise sales

CRM/MAP proficiency

Team building

Tools

Salesforce

ActiveCampaign

Job description

Position: Director, Enterprise Sales

Location: Kanata (Hybrid)

Reporting to: Angela Hunt

Meet Cliniconex

At Cliniconex, our focus is our customers, our community and our culture. As a small company, we understand the importance of having a team that connects effectively. Whether it’s day-to-day operations or an emergency, teams need to be on the same page, and that’s why we make healthcare communication and collaboration solutions that are as easy as 1,2,3. Easy to implement, easy to use and easy to scale. Our solution reaches audiences via voice, text or email, strengthens teams with a record of all conversations, and unites a family-centered community through timely, transparent outreach. The result? More time to care.

What You’ll Be Doing

As the Director, Enterprise Sales at Cliniconex, you'll play a vital role in driving growth and revenue through direct sales into the mid-market and enterprise segments, including marketplace partnerships. Reporting directly to the Chief Revenue Officer, you'll lead a team of two Enterprise Sales Account Managers, one SMB Account Manager, and a contract team of Sales Development Representatives (SDRs), shaping and executing sales strategies that empower our teams to exceed targets and expand Cliniconex’s footprint across the mid-market and enterprise markets. This is a high-impact role where your leadership will contribute directly to our mission of delivering exceptional value to our partners and customers.

Your Responsibilities

• Own the enterprise sales cycle end to end, from pipeline development and qualification through to contract execution, with clear forecasting discipline at every stage.
• Identify, qualify, and lead RFP, RFI, and RFQ opportunities, coordinating internal contributors and ensuring every submission is complete, compelling, and on time.
• Direct the contract SDR team on outbound targeting, messaging, and meeting quality for mid-market and enterprise accounts.
• Collaborate with Marketing, Customer Success and Product teams to enhance lead generation and improve conversion rates in the mid-market and enterprise segments.
• Establish performance metrics, track progress, and optimize sales processes to improve efficiency and effectiveness across teams.
• Serve as the closer for high-value deals, providing support to the team with final pricing, contract negotiation, security and procurement reviews, and deal closure.
• Provide insights and recommendations to the Chief Revenue Officer based on market trends, competitive landscape, and sales performance data.
• Leverage CRM/MAP tools and analytics to monitor sales performance and identify opportunities for improvement.

What We’re Looking For

• Has 7+ years of sales leadership experience, preferably in mid-market or enterprise B2B software sales.
• Has a proven track record of moving an organization upmarket, growing sales from SMB into the mid-market and enterprise segments, and building the processes and discipline required to support it.
• Has contributed directly to scaling revenue toward a $50M business, and understands what changes at each stage of that growth.
• Is experienced in sourcing, qualifying, and submitting RFPs, including managing multi-stakeholder procurement, security, and compliance reviews.
• Demonstrates a proven track record of success in managing and scaling high-performing sales teams.
• Exhibits excellent leadership, coaching, and mentoring skills with the ability to inspire and motivate teams.
• Possesses strong strategic thinking and analytical skills, with the ability to translate data into actionable insights.
• Is experienced in developing go-to-market strategies for mid-market and enterprise buyers, and in building productive marketplace partnerships.
• Has exceptional communication, negotiation, and relationship-building skills.
• Is proficient in using CRM/MAP software (e.g., Salesforce, ActiveCampaign) and other sales productivity tools.

Bonus Points for

• Experience with reseller relationships, including supporting reseller channel sales teams on mid- to large-size deals.
• Established relationships with channel sales leaders, and a track record of maintaining and growing them over time.
• Experience working in the healthcare technology or SaaS industry.
• Familiarity with sales enablement tools and best practices.
• Prior experience working closely with Marketing, Customer Success and Product teams to drive go-to-market initiatives.

Compensation

• $125,000 - $135, 000 CAD base with a bonus structure

Perks of Joining Our Team

• Make a Real Impact: Join a mission-driven team that's transforming patient care across North America. Your work will directly contribute to better health outcomes and meaningful change.
• Flexible Hybrid Work Model: We believe in balance. Enjoy the best of both worlds with a mix of remote work and in-office collaboration.
• 30 Days of Paid Time Off: Work hard, rest well. We offer a generous PTO policy to support your work-life balance - right from the start.
• Health & Wellness Budget: Invest in your well-being with an annual budget to support your physical, mental or emotional health.
• Internet Budget: We provide a budget for home internet expenses so you can stay connected and productive while working from home.
• Collaborative Culture: Be part of a supportive, dynamic team where every voice is heard, and innovation thrives.
• Growth & Development: We're committed to your success and encourage you to learn and grow your skills
• Day-One Benefits & Flexibility: Enjoy comprehensive benefits on your first day!

Equal Opportunity and Accommodations

Cliniconex is an equal opportunity employer. We encourage applications from individuals of all backgrounds, races, genders, abilities, and identities.

Accommodations will be provided at all stages of the selection process. Please contact [e-mail] for any accommodation requirements.