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Senior Director, Data Science and Machine Learning

Build your career at a tech company solving a real-world problem: the tedious and manual process of responding to RFPs. Help us innovate in the proposal space—and grow your career in the process.

Loopio is a workplace that unleashes learning & growth opportunities for our Loopers. We provide autonomous, challenging work that allows each employee to master their craft. We attract and retain people who are naturally curious, have grit and are eager to grow and build their careers. At Loopio, we genuinely support each other, because true success comes from working as #oneteam.


Loopio’s Data Enablement Team works together on a mission to transform the RFP response process into a rapid and seamless experience. Our team works across all platform portfolio features and delivers innovative solutions where it matters the most for our customers. 


We are looking for an experienced Senior Director, Machine Learning and Data Science, to lead a dynamic group of Machine Learning Engineers, Data Scientists, and Data Engineers on our Data Enablement team.  Our ideal candidate has deep technical and leadership experience building ML/AI commercial products and is comfortable working in an evolving and dynamic environment. This is a unique opportunity to join a growing team of creative and passionate individuals committed to solving real-world problems. 


Reporting to the Chief Product Officer, you will partner closely with our Senior Product Leaders and business stakeholders across Loopio to drive leadership in data and AI innovation.

What You’ll Be Doing

  • You will be a valuable member of the Senior Product Leadership team and, as such, responsible for fostering a thriving culture, product execution and innovation. 

  • Lead the development of advanced automation tooling for data orchestration, evaluation, testing, monitoring, administration, and data operations.

  • Inspire and lead the Data Enablement team, which includes Machine Learning Engineers, Data Scientists and Data Engineers, by setting clear objectives, promoting innovation, and ensuring alignment with the company’s strategic goals.

  • Responsible for creating a high-performing team and fostering a culture of technical excellence, continuous improvement, and collaborative problem-solving within the team. 

  • Lead with company values in mind and help create bridges across organizations. 

  • Lead the development of scalable data pipelines using Databricks, and AWS (Redshift, S3, RDS), and other cloud technologies. 

  • Build, deploy and operate production ML models to power many aspects of our product experience.

What You’ll Bring to the Team

  • 4+ years of experience in leading and growing high-performing machine learning or data science teams in fast-paced environments. 

  • Deep expertise in machine learning or data science. Demonstrable experience with advanced ML algorithms and frameworks, as well as NLP/NLU are essential. 

  • Experience building, deploying and operating ML/AI-powered customer-facing products at scale.

  • Strategic Problem-Solving skills with the ability to align  technical/engineering principles with business priorities

  • Proficient in distributed systems development using a microservices architecture, and Public Cloud platforms

  • Prior experience in Data Warehousing (EDW), with a solid grasp of Data Lake architecture and design. 

  • Skilled in designing and implementing cloud-based training pipelines and state-of-the-art deep learning algorithms.

  • Demonstrated ability in delivering large-scale, customer-facing, and mission-critical products, ideally in agile, high-growth B2B SaaS environments. 

  • Exceptional communication and interpersonal skills, with the ability to articulate technical roadmaps, challenges, and solutions effectively across cross-functional teams. 

  • Proven ability to inspire and positively influence others, leading teams through complex or ambiguous situations.

  • Strong business acumen with an understanding of total cost of ownership and cost-to-profitability models across multiple interdependent products.

  • Experience in building and maintaining large-scale systems in production environments.

Bonus Qualifications

  • Experience with container orchestration (leveraging tools like Docker, ECS, Kubernetes)

  • Experience working with BI PaaS / SaaS solutions

  • Familiarity with microservice architectures 

  • Hands-on experience as ML/DS Engineer

  • Experience with Natural Language Processing techniques

  • Experience using deep learning frameworks such as TensorFlow / Pytorch

Where You’ll Work

  • Loopio is a remote-first workplace because we recognize the advantages of working flexibly. We have Hub Regions spanning across Canada, UK, and India, which means that employees live and work remotely within a 300 KM radius of Toronto (within Ontario),Vancouver (within British Columbia), Ahmedabad (within Gujarat), Pune (within Maharashtra), and London (UK) and work within regular business hours in their timezone. 

  • Loopio has two flexible co-working locations available to Loopers in ON and BC. Those based in ON have the flexibility of working out of our convenient coworking space located in the heart of Downtown Toronto and a 12-minute walk from Union Station. BC Loopers have the option to work from our co-working office in Gastown Vancouver. It is whatever works best for you!

  • You’ll collaborate with your teams virtually (we’re just a Zoom call away!) and have established core sync hours and focus time during the workday to enable us to work smarter together

Why You’ll Love Working at Loopio

  • Your manager supports your development by providing ongoing feedback and regular 1-on-1s 

  • You have tons of autonomy and responsibility: this role provides an opportunity to try new things and push creative boundaries

  • You’ll learn more than you thought was possible; our team is obsessed with personal and professional growth (every Looper receives a professional mastery allowance each year)

  • You’ll be set up to work remotely with a MacBook laptop, a monthly phone and internet allowance, and a work-from-home budget to help get your home office all set up! 

  • Join us in regular company socials, AMA (Ask-Me-Anything), and quarterly kick-off to celebrate the big wins and milestones as #oneteam!

  • You’ll be joining a culture that has thoughtfully built out opportunities for connections in a remote first environment.

  • We have Employee Resource Groups, various fun virtual activities, and many more moments for us to have fun and learn together! 

  • You’ll be a part of an award-winning workplace and one of Canada’s fastest growing companies with ample opportunity to make a big impact here!

We recognize that all too often, potential candidates don’t apply for a position simply because they don’t hit every single criteria included in the job description—particularly members of underrepresented groups


Whether or not your experience checks off all the boxes on a job posting, we still encourage you to apply to ensure that your application receives a review from our team. We understand that a resume can only showcase so much during the applicant stage, so we've created prompts in the application for you to share more about yourself. If you've made a career transition (or a few!), you’re self taught in a new role, or you have skills/experience you’d like to highlight, we want to hear more about what you could bring to the table.


Loopio is an equal opportunity employer that is deeply committed to building equitable workplaces that are diverse and inclusive. We actively encourage candidates from all backgrounds and lifestyles to consider us as a future employer. Please contact a member of our Talent Experience team (work@loopio.com) should you require accommodations at any point during our virtual interview processes.

Average salary estimate

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What You Should Know About Senior Director, Data Science and Machine Learning, Loopio Inc.

If you're excited about solving real-world problems through data science and machine learning, then the role of Senior Director, Data Science and Machine Learning at Loopio might be just what you're looking for! At Loopio, we take pride in our vibrant and dynamic workplace, where we encourage every Looper to master their craft while working on innovative solutions that transform the RFP response process. In this pivotal role, you'll lead our talented Data Enablement Team, composed of Machine Learning Engineers, Data Scientists, and Data Engineers, driving innovation and collaboration across our platform. Your leadership will be crucial as you develop cutting-edge automation tools, scalable data pipelines using technologies like Databricks and AWS, and deploy production ML models that enhance our product experience. You'll partner closely with our Chief Product Officer and senior product leaders, nurturing a culture of technical excellence and continuous improvement. With over four years of experience leading high-performing teams in fast-paced environments and deep expertise in machine learning, you will inspire innovation and ensure alignment with our strategic goals. Join us and help shape the future of data science at Loopio—all while enjoying the flexibility of our remote-first workspace and a culture that truly supports personal and professional growth.

Frequently Asked Questions (FAQs) for Senior Director, Data Science and Machine Learning Role at Loopio Inc.
What are the responsibilities of the Senior Director, Data Science and Machine Learning at Loopio?

The Senior Director, Data Science and Machine Learning at Loopio is responsible for leading the Data Enablement team, which encompasses Machine Learning Engineers, Data Scientists, and Data Engineers. This role involves developing advanced automation tooling for data orchestration and building scalable data pipelines using tools like Databricks and AWS. Additionally, you will foster a culture of innovation within your team and collaborate with business stakeholders to drive AI and data innovation aligned with Loopio's strategic goals.

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What qualifications are required for the Senior Director, Data Science and Machine Learning position at Loopio?

To qualify for the Senior Director, Data Science and Machine Learning role at Loopio, candidates should have over four years of experience leading high-performing teams in machine learning or data science. Proficiency in advanced ML algorithms, experience with deploying ML-powered products, and a solid grasp of distributed systems development and cloud platforms are vital. Strong communication and interpersonal skills, alongside a strategic mindset, are also essential for success in this role.

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How does Loopio support the growth of its Senior Director, Data Science and Machine Learning?

At Loopio, we are deeply committed to continuous personal and professional growth for all employees, including the Senior Director, Data Science and Machine Learning. You will receive ongoing feedback from your manager and regular one-on-ones, ensuring your development is prioritized. Additionally, every Looper receives a professional mastery allowance each year, enabling you to pursue opportunities for growth tailored to your career aspirations.

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What technologies will the Senior Director, Data Science and Machine Learning at Loopio be working with?

In the role of Senior Director, Data Science and Machine Learning at Loopio, you will predominantly work with cloud technologies such as AWS (including Redshift, S3, and RDS) and Databricks for scalable data pipeline development. Your expertise in machine learning frameworks, particularly those for natural language processing and deep learning, will also be leveraged to enhance our product experience.

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What is the company culture like at Loopio for the Senior Director, Data Science and Machine Learning role?

The company culture at Loopio is built on collaboration, support, and innovation. As a Senior Director, you will join a team that genuinely cares about professional growth and encourages an autonomous work environment. Loopio promotes a remote-first culture, offering flexibility and numerous virtual activities, and aims to build connections through Employee Resource Groups and regular social events.

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Common Interview Questions for Senior Director, Data Science and Machine Learning
Can you describe your experience in leading data science teams?

In your response, highlight specific experiences where you've successfully led data science teams. Discuss the size of the teams, the projects you managed, and how you fostered a culture of collaboration and innovation. Be sure to mention any challenges faced and how you overcame them to achieve your goals.

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What machine learning algorithms are you most comfortable with, and how have you applied them?

Talk about the specific machine learning algorithms you are well-versed in and provide examples of projects where you successfully implemented them. Explain your thought process behind choosing particular algorithms and the results achieved through their application.

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How do you ensure effective communication between technical and non-technical stakeholders?

Discuss strategies you use to bridge communication gaps, such as simplifying complex concepts into layman's terms or using visuals to explain data insights. Highlight instances where clear communication led to successful collaboration across teams.

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Describe a time when you had to deploy production ML models. What challenges did you face?

Reflect on specific situations involving the deployment of ML models, including the challenges faced, such as integration issues or performance concerns. Give details on how you resolved these challenges and what you learned in the process.

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What strategies do you utilize for developing scalable data pipelines?

Outline your approach for building scalable data pipelines, discussing the technologies and frameworks you prefer, such as AWS and Databricks. Consider mentioning how you optimize for performance and troubleshoot issues that arise during the process.

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How do you inspire innovation within your data science team?

Share techniques for fostering a culture of innovation, such as encouraging open brainstorming sessions, offering professional development opportunities, and recognizing team members’ contributions. Provide examples of how this approach has led to successful outcomes.

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What experience do you have with cloud-based data services?

Discuss your hands-on experience with cloud platforms like AWS or Azure. Sharing specific projects where you utilized these platforms to build or manage data solutions will demonstrate your technical proficiency and ability to navigate cloud-based environments effectively.

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Can you give an example of a successful machine learning project you have led?

Provide a detailed case study of a machine learning project, highlighting the objectives, strategies employed, the team involved, and the impact of the project. Focus on key metrics and business outcomes achieved as a result of the project.

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How do you stay updated with advances in machine learning and data science?

Explain how you engage in continuous learning, referencing any courses, certifications, conferences, or professional networks you participate in. Emphasizing your commitment to ongoing education demonstrates your dedication to both your personal and professional development.

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What is your approach to mentoring junior data science team members?

Discuss your mentoring philosophy and approach to helping junior team members grow. Provide specific examples of mentorship experiences, focusing on how you've helped them develop their skills and navigate challenges in their careers.

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Founded in 2014, Loopio offers a RFP response solution which streamlines the way enterprises respond to Requests for Proposals (RFPs), Requests for Information (RFIs), Due Diligence Questionnaires (DDQs), and Security Questionnaires. The company i...

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Full-time, remote
DATE POSTED
January 3, 2025

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