Now hiring
Director of Learning (Strategy, Transformation, and Innovation)
Now hiring

Director of Learning (Strategy, Transformation, and Innovation)

About Toptal

Toptal is a global network of top freelance talent in business, design, and technology that enables companies to scale their teams, on-demand. With $100+ million in annual revenue and over 40% year-over-year growth, Toptal is the world’s largest fully remote company.

We take the best elements of virtual teams and combine them with a support structure that encourages innovation, social interaction, and fun. We see no borders, move at a fast pace, and are never afraid to break the mold.

Position Description

Toptal is in hyper growth mode, so we are constantly onboarding new hires and working with our existing team members to enhance and develop their skills. As the newly created Director of Learning Experience Design, you and your team will work with leaders and individual contributors to identify opportunities to build learning plans and materials to achieve company goals. You will develop deep institutional knowledge of the core skills needed for key positions across Toptal, thinking critically about innovative ways to elevate the abilities of team members across the organization.

As an expanding function, we are striving to build comprehensive learning programs that will include rigorous professional and skill development, a robust onboarding experience for new team members, and ongoing support across the organization. You will lead the team in establishing and monitoring KPIs to measure effectiveness and scale programs. Your team will support a variety of functions, including highly technical teams - demonstrated experience supporting engineering and product teams is preferred.

This is a remote position that can be done from anywhere. Due to the remote nature of this role, we are unable to provide visa sponsorship. Resumes and communication must be submitted in English.


As the Director of Learning (Strategy, Transformation, and Innovation), you will be responsible for building a world-class learning function that enables Toptal’s core team members to be on the cutting edge of their respective fields and continuously hone their skills to maximize their potential. You will own Toptal’s learning and development programs end-to-end, including designing the strategy, establishing operating models and processes, measuring results, and scaling our Core Team.

You will work with leadership across the company to identify how learning and development can support their teams in achieving business objectives. You will be responsible for leading your team in designing, developing, and delivering effective and engaging learning interventions that impact performance. You will work as a part of the People team to evaluate the efficacy of our learning initiatives, build new strategies based on feedback and analysis, and evolve.

In the first week, expect to:

  • Rapidly begin learning about Toptal’s history, culture, and vision.
  • Learn about Toptal services, learn about Toptal’s organizational structure, including each team’s focus and how they interact.
  • Begin meeting with senior leaders across the company.

In the first month, expect to:

  • Deep dive in Toptal’s current and future learning programs, including reviewing why they exist, their strengths and opportunities, and their impact.
  • Begin to develop and build a short-term and long-term learning strategy.
  • Begin working with senior leaders to identify and prioritize opportunities.

In the first three months, expect to:

  • Set a long-term vision for world-class professional development at Toptal that allows the elite Core Team to stay on the cutting edge of their fields and perform at the highest levels of client service.
  • Build solutions and adapt your approaches in real-time by incorporating feedback and shifting priorities.

In the first six months, expect to:

  • Work with the analytics team to develop metrics that demonstrate the impact of your team’s learning programs and strategy.
  • Develop strategies that engage and motivate core team members, building the foundation of a learning organization.

In the first year, expect to:

  • Demonstrate the significant impact of your team’s learning programs through a variety of metrics.
  • Build the foundation to scale your team into a world-class learning function.


  • 10+ years in a global professional learning and development environment, with advanced experience developing blended learning programs, self-directed, instructor-led training (ILT), computer-based training (CBT), and webinar training.
  • 5+ years of leadership experience with responsibility for business results in a fast-paced, multi-function environment.
  • Strong experience managing or building a framework to measure learning outcomes and effectiveness for a variety of scenarios - ability to understand, analyze, and communicate learning data.
  • You must be forward-thinking, motivated by continuous improvement, and be excited to impact the skills of core team members.
  • Demonstrated experience in a large tech-oriented enterprise - experience at an early stage learning organization is a plus.
  • Experience supporting technical engineering teams is highly preferred.
  • Significant strategic research and analysis experience with a strong understanding of how to build a compelling, data-driven business case.
  • Resourcefulness. You must refuse to be impeded by anything standing in your way. You must push to get access to any resources you need, contribute unsustainable effort when the situation calls for it, and be creative in finding ways to remove blockers and deliver value.
  • Adaptability. You should be able to identify opportunities, successes, and failures quickly and act upon them in a thoughtful manner.
  • Passion. Our goal is to change the way organizations build teams and how the world’s top Core Team finds opportunities. You have to be passionate about what we do, and be a strong advocate of the change we are driving in the market.
  • Communication. Must be a strong communicator able to speak to a wide range of stakeholders and team members, across a wide range of geographies.
  • You must be a world-class individual contributor to thrive at Toptal. You will not be here just to tell other people what to do.
For Toptal Use Only: #west #midwest #ussouth #northeast #canada #westerneurope #LI-LP2 #LI-REMOTE

Who You Will Work With

Michelle Labbe

Michelle Labbe

Chief People Officer

As Toptal's Chief People Officer, Michelle is accountable for our People and Recruiting teams, creating and maintaining a world-class experience for all Toptal team members through hiring, developing, and retaining our top talent. Previously, she served as Chief People Officer at ICR. Her 20+ year career has included senior Talent leadership roles across both the startup and agency world, spanning multiple industries. Michelle has a Bachelor’s in Political Science from the University of Arizona.

Christy Schumann

Christy Schumann

VP of Talent Operations

As Toptal's VP of Talent Operations, Christy is accountable for ensuring successful client outcomes by delivering the right talent from our global network, matched to client business needs and timeframe. Prior to Toptal, Christy spent more than a decade in management consulting at Bain & Company, and she later joined Rackspace as General Manager of their cybersecurity business. Christy earned a BS in Computer Science and Electrical Engineering from the Massachusetts Institute of Technology and an MBA from Columbia Business School.

Ismael Peinado

Ismael Peinado

Chief Technology Officer

As Toptal's Chief Technology Officer, Ismael leads the company's engineering organization, driving process and culture to ensure top quality delivery from our team of world-class engineers. Ismael was formerly the CEO and Co-Founder of Blue4, a distributed media system used in the aerospace and entertainment industries. He leverages over twenty years’ experience in providing commercial, operational, and technical leadership for B2B, B2C, and government organizations from early-stage startup to large-high growth market leaders. Ismael has a BE and BS in Industrial Engineering from the Universidad de Málaga.

View The Whole Team

Working at Toptal

We're changing the way the world works. Toptal is not only a place to progress your career and design your own lifestyle, but also a company where you'll learn how to develop innovations that push business and technology forward.
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Think you’re a fit? Apply below:


How many years of leadership experience do you have?

How many years of experience do you have working in a corporate environment within an L&D function, developing blended learning programs, self-directed, instructor-led training (ILT), computer based training (CBT), and webinar training?

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Working at Toptal has been the best experience of my career. Every day I'm surrounded by intelligent, thoughtful, and hard-working colleagues that push me to be better.

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