Senior Director of Operations

TripStack; Old Toronto; On-site; CAD 90,000 - 150,000; Full time

Job summary

Join a forward-thinking company as a Senior Director of Operations, where you'll shape client experiences and drive operational excellence. This dynamic role bridges sales and delivery, ensuring seamless transitions and exceptional service. With a focus on strategic goals and productivity, you'll lead a talented team in a fast-paced environment, making a real impact in the travel tech industry. If you're passionate about innovation and eager to contribute to a mission-driven team, this is the opportunity for you to thrive and grow.

Benefits

Dynamic Work Environment

Professional Development Opportunities

Diversity and Inclusion Initiatives

Qualifications

• 10+ years in operations or client success, preferably in travel or tech.
• Strong organizational skills and ability to manage complex projects.

Responsibilities

• Lead client onboarding and ensure smooth transitions to operations.
• Analyze operational processes and recommend improvements.

Skills

Operations Management

Client Success

Leadership Skills

Problem-Solving

Communication Skills

Project Management

Education

Bachelor's Degree

Master's Degree (preferred)

Job description

About TripStack

We are travel tech entrepreneurs, changing the way millions of people travel.

Our proprietary virtual interlining technology provides access to billions of travel itineraries by combining flights from different airline carriers that don’t traditionally work together. We take our customers from point A to B via C, at the lowest possible price. We are impacting the way people travel and provide higher margin opportunities to our partners that are some of the largest in the travel industry.

We pride ourselves on the performance-driven environment we have created for our teams to prosper and excel in. We come to work ready, to challenge and be challenged. We’re big enough to give our teams support but small enough that every person makes a difference. There are plenty of challenges to champion.

The Role

As the Senior Director of Operations, you will play a pivotal role in shaping how TripStack serves its clients. Reporting directly to the CEO, you will bridge the gap between sales and client delivery, ensuring smooth handovers, exceptional service delivery, and long-term client satisfaction. This role requires exceptional organizational skills, and the ability to collaborate with internal and external stakeholders. The senior director of operations will develop long-term plans that usher in new levels of productivity and success for the company.

Responsibilities:

• Act as the primary point of contact during the sales-to-operations handover process, ensuring all client requirements and expectations are clearly communicated and documented.
• Set strategic goals for operational efficiency and increased productivity.
• Lead the onboarding of new clients, ensuring a seamless transition to post-go-live operations.
• Analyze current operational processes and performance, recommending solutions for improvement where necessary.
• Develop, implement, and monitor day-to-day operational systems and processes to provide visibility into the goals, progress, and obstacles of key initiatives.
• Maximize efficiency and productivity through extensive process analysis and interdepartmental collaboration.
• Monitor client projects post-go-live to ensure timelines, deliverables, and KPIs are met.
• Establish strong relationships with clients to understand their evolving needs and ensure their success with TripStack’s technology.
• Serve as a strategic partner to clients, offering creative solutions to challenges as they arise.
• Devise strategies for ensuring the growth of programs enterprise-wide, and implement process improvements to maximize output and minimize costs.
• Collaborate with cross-functional teams (sales, product, engineering) to drive cohesive client success strategies.

Desired Skills and Experience:

• 10+ years of experience in operations, client success, or professional services, with a proven track record in the travel industry or technology sector.
• Masterful communication and leadership skills, backed by previous professional success.
• Strong organizational and problem-solving skills, with a focus on scalable solutions.
• Demonstrated ability to manage complex projects, navigate ambiguity, and prioritize competing demands for maximum efficiency and productivity.
• Experience in a startup or tech environment, comfortable working in fast-paced, dynamic settings.
• Exceptional stakeholder management and relationship-building skills, with a client-first approach.
• Excellent verbal and written communication skills, capable of influencing at all organizational levels.
• Ability to streamline or implement structures and roles that boost speed and efficiency while supporting rapidly shifting business demands.

Additional experience that would be considered an asset:

• Deep understanding of the travel ecosystem, including airlines, GDS, OTAs, or other travel technology companies.
• Knowledge of virtual interlining, professional services, or travel product delivery is a strong asset.

What it takes to succeed here

Ambition and dedication to make a difference and change the way people travel; where we always play to each other's strengths in a high-performing team reaching for our common goal. We hold ourselves to the highest expectations, move with a sense of urgency, and hold ourselves accountable while staying true to what we believe in.

What we offer

We offer an opportunity to work with a young, dynamic, and growing team composed of high-caliber professionals. We value professionalism and promote a culture where individuals are encouraged to do more and be more. If you feel you share our passion for excellence and growth, then look no further. We have an ambitious mission, and we need a world-class team to make it a reality. Upgrade to a First Class team!

At TripStack, we proudly believe in embracing diversity. This is true for our team, clients, communities, and stakeholders. We are an equal opportunity employer and committed to creating a safe, healthy, and accessible environment. We encourage applications regardless of race, colour, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, or any other grounds protected by law. Please let us know if you need any accommodations during any part of the recruitment process.

TripStack thanks all applicants for their interest; however, only those selected to continue in the process will be contacted.

Learn more about us at www.tripstack.com

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