Sales Executive (Calgary, AB)

From our Calgary HQ to our teams in Edmonton, Red Deer, and the Okanagan, SysGen helps businesses across Western Canada boost productivity, security, and growth. Our Dedicated IT Support Model® means we build real relationships with clients, not just fix tickets. Guided by our 8 principles of collaboration, innovation, integrity and more, we tackle serious IT challenges but always as a team. Join us and you’ll troubleshoot, innovate and celebrate wins together, making IT more effective and way more fun.

Do you love connecting with people, spotting opportunities, and making things happen? As a Sales Executive (Client Experience Specialist), you’ll be the driving force behind helping our clients grow – and helping SysGen grow right alongside them. You’ll lead the charge in turning great service into lasting partnerships, uncovering ways technology can boost performance, productivity, and success. If you’re energized by relationship-building, business growth, and making a real impact, this is your chance to join a team that’s passionate about people, powered by technology, and committed to helping SMBs thrive in a digital world.

At SysGen, you’re not just starting a job; you’re logging into a team that’s wired for collaboration, cloud-level fun, and big ideas that never crash.

Life at SysGen – Perks & Benefits (What’s in it for you?)

• Earn More: Competitive salary plus performance-based compensation.
• Vacation Your Way: Take advantage of our unique Double Dip vacation program.
• Live Well: Work-life balance with a hybrid work schedule, comprehensive benefits, and a culture of health & wellness.
• Culture that Clicks: From team-building activities (that are actually fun) and Fun Fridays to staff appreciation and company-wide celebrations, we create moments that bring people together.
• GetRewarded: EVERYONE is eligible to win President’s Club and join an all expenses paid trip (the trip last time it was to Mexico!)
• Grow Your Career: Paid training and development to help you level up.
• Make Your Mark: We’re a flat organization where your ideas matter. No red tape, no endless approvals; just the freedom to create impact and make meaningful changes right away.
• Join a Winning Team: SysGen is diverse, innovative, and recognized with multiple awards, such as:
• Top Managed Services Provider by Channel Futures (Last 4 consecutive years)
• Cloud Tango’s Top Managed Service Providers Canada (Last 2 consecutive years)
• Canada’s Top 100 & MSP500 Small & Medium Employers (7 Years in a row)
• Canada’s Top Growing Companies by The Globe and Mail (3 Years)

Key Responsibilities

• This is a revenue-focused role combining sales and account management within an existing client base, you’ll grow accounts through upsell and cross-sell opportunities while building strong, long-term relationships (no cold outreach required).
• Own and grow a portfolio of diverse clients, driving retention, expansion, and satisfaction through proactive relationship management and value-driven sales strategies.
• Develop a deep understanding of each client’s business goals, uncovering opportunities to align SysGen’s IT solutions with their evolving needs and long-term strategy.
• Lead and present Business Reviews for Managed Services clients that highlight performance and risks, recommend improvements, and position new services, upgrades, and technologies that align IT strategies with the client’s business goals in clear, client-friendly language.
• Proactively identify and pursue upsell and cross-sell opportunities, leveraging data insights and client conversations to recommend high-impact solutions.
• Engage Time & Material (T&M) clients to strengthen relationships, promote managed service options, and convert ad-hoc work into recurring partnership opportunities.
• Collaborate closely with IT Managers and internal teams to support clients in maintaining and optimizing their IT budgets, forecast future needs, and present business cases for new technologies or service enhancements.
• Act as the client advocate within SysGen, ensuring their voice is heard and satisfaction remains high while balancing business growth goals and maintaining strong internal alignment.
• Negotiate renewals, service expansions, and contract adjustments, ensuring clients clearly understand the value and ROI of SysGen’s offerings.
• Maintain accurate sales forecasts, pipeline activity, and client notes in CRM tools to track performance and inform business planning.
• Develop strong, lasting relationships with decision-makers and stakeholders through consistent communication, follow-up, and a deep understanding of their business priorities.
• Champion SysGen’s brand and capabilities by articulating our competitive advantages and reinforcing our commitment to customer service excellence.
• Uphold SysGen’s 8 Guiding Principles in every interaction to ensure ethical, transparent, and relationship-driven business growth.

Knowledge and Skill Requirements

• Degree or Diploma in Business Administration, Commerce, or Information Management, or equivalent experience.
• Strong understanding of account management, client retention, and sales growth strategies within a B2B or service-based environment.
• Proven ability to identify, position, and close upsell and cross-sell opportunities through consultative conversations.
• Demonstrated experience in presenting complex technical or performance information in a clear, client-friendly way.
• Solid grasp of IT managed services concepts, including infrastructure, cloud solutions, cybersecurity, and user support – is an asset
• Excellent relationship-building and communication skills with the ability to engage confidently with executives, business owners, and technical teams.
• Skilled in strategic problem-solving and able to translate business challenges into actionable technology and service solutions.
• Proficient in CRM tools and sales pipeline management, with strong organizational and follow-up habits.
• Ability to analyze client data and performance trends to inform business discussions and identify growth opportunities.
• Strong presentation and negotiation skills, with comfort leading client meetings, proposals, and renewal discussions.
• Collaborative mindset who thrives in a team-based environment with technical, operations, and leadership colleagues.
• Commitment to delivering exceptional client experiences, embodying SysGen’s service-first philosophy.
• Highly self-motivated, target-driven, and adaptable, with a focus on continuous learning and improvement.

SysGen employees are guided by our 8 Guiding Principles:

Interested in applying and learning more about SysGen?

SysGen follows the principles of equal opportunity, diversity, and inclusiveness regarding our hiring and promotion procedures.