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Director of Effectiveness Strategy, Enterprise
Now hiring

Director of Effectiveness Strategy, Enterprise

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 $200+ 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

As the Director of Effectiveness Strategy at Toptal, you are responsible for developing and maintaining the sales effectiveness plan and coordinating its implementation to support the continued growth of our Enterprise business. You will partner closely with the Enterprise senior leadership team and Revenue stakeholders to ensure the team’s growth needs are effectively reflected and executed in an integrated development and enablement plan.

This role is perfect for someone who is energized by a fast-paced, high-growth environment, is highly organized, demonstrates exceptional attention to detail, and excels in cross-functional communication and alignment.

Day to day, you’ll work closely with the Enterprise senior leadership team, Enterprise Enablement and Effectiveness, Enterprise Operations, and cross-functional business partners. While doing so, you should be comfortable navigating ambiguity to arrive at a positive outcome, while remaining agile in your operating approach. Your deep discovery and prioritization will enable greater alignment on key focus areas and the respective success criteria. Being comfortable making swift progress, rather than holding out for perfection, will be one of the keys to your success in this role and to drive transformational change in the business.

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.


We are looking for someone who is passionate about driving a cohesive effectiveness plan for our fastest growing sales division; collaborating on and organizing an integrated plan rather than a collection of ideas. You should excel in developing a system for validating, organizing, and prioritizing needs to fuel the team’s current and future development.

Major responsibilities will include:

Effectiveness strategy development: You will collaborate with the Enterprise senior leadership team, the Revenue Effectiveness and Enablement team, and additional cross-functional partners to develop, maintain and execute the effectiveness strategy and plan for the year, balancing between the business’s current and future needs. As you excel in your role, you will reveal areas of opportunity and architect solutions with your stakeholders. You will influence the quarterly themes and creative approaches for delivery with the ultimate goal of driving revenue growth while maximizing client-facing time.

Roadmap management: You will own the management, administration, and communication of Enterprise’s effectiveness and enablement roadmap, ensuring the timing of launches and resources are considered in relation to goals and bandwidth. You will collaborate cross-functionally to ensure the details for each release are complete and ready to launch on time. This includes working collaboratively across the wider Effectiveness and Enablement team, cross-functionally, and with project managers to ensure priorities are executed upon in a timely manner.

Requests management: You will design and maintain a framework to accept and prioritize new requests to and from Enterprise leadership. Understanding the “opportunity to seize” or “problem to solve” while balancing the return on investment, you’ll influence how new requests are integrated into the roadmap. Given the volume of requests, remaining objective and highly data-driven in your approach will enable you to effectively recommend prioritization of new requests to your stakeholders and further ensure the requests are tied to measurable KPIs.

Strategy communication: You will own communication of the effectiveness strategy plan to the Enterprise leadership team for awareness and input. For proactive resource allocation and planning, you will own Enterprise strategy communication cadences with the wider Enablement and Effectiveness team. You’ll lead cadences with the wider Effectiveness and Enablement leadership team to ensure full alignment on needs, timing, and the plan to achieve.

The ideal candidate is highly driven, analytical, organized, and collaborative, and has a strong track record of partnering with multiple business stakeholders to achieve measurable revenue goals.

In the first week, expect to:

  • Onboard and integrate into Toptal.
  • Rapidly begin learning about Toptal’s history and vision.
  • Familiarize yourself with the Revenue team’s OKRs, initiatives, projects, and how they are aligned to Toptal’s overall success.
  • Meet the Revenue Team and your key stakeholders to begin uncovering individual and team priorities.

In the first month, expect to:

  • Learn the true value of Toptal by completing onboarding training, shadowing calls, and meeting with key stakeholders.
  • Explore Toptal’s tools and resources to understand how they are currently used.
  • Familiarize yourself with Enterprise’s priorities, goals, and initiatives.
  • Join key Enterprise business meetings to become familiar with weekly rhythms of the Enterprise leadership team.
  • Shadow ongoing projects to become familiar with your cross-functional team and project plans at Toptal.

In the first three months, expect to:

  • In partnership with Enterprise leadership, build and manage the effectiveness roadmap.
  • Lead communications on the roadmap including proposed add/modifications.
  • Formalize a high-functioning, agile process to consolidate and prioritize all stakeholder requests for the Effectiveness and Enablement Team.
  • Begin to identify areas for improvement and additional opportunities.

In the first six months, expect to:

  • Make significant progress on execution plans, as evidenced by the achievement of post-launch initiative milestones and KPIs.

In the first year, expect to:

  • Own or assume a key role in designing how effectiveness moments are delivered, communicated and measured to Enterprise to drive one of the highest growth rates in the industry.


  • 8+ years combined business operations and consulting experience.
  • At least 1 year working for a major consulting firm with expertise in development of strategic operational frameworks and executive presentations.
  • Leadership experience with responsibility for business results in a fast-paced, multi-function environment.
  • Creative problem solver with proven results in improving processes in a business operations and/or sales environment.
  • Ability to leverage data to perform root cause analysis and address the source of issues.
  • Proven ability to develop creative solutions that result in measurable transformative outcomes that reach beyond incremental improvements.
  • Strong collaboration skills and demonstrated ability to influence and execute effectively in a cross-functional environment.
  • Impeccable organization skills and attention to detail.
  • Ability to apply effective change management principles and consider the human element of change.
  • A knack for being able to convey complex information and recommendations in a clear, logical, understandable manner to stakeholders at executive levels.
  • Excellent presentation, written, and verbal communication skills.
  • Must be a high integrity, team player with flexibility to meet the demands of changing business priorities.
  • 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.
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Who You Will Work With

Sean Middleton

Sean Middleton

Chief Revenue Officer

As Toptal's Chief Revenue Officer, Sean is responsible for strategy, sales, and client success. He works closely with the executive team to ensure their growing client portfolio has access to the best talent in the world. Before joining Toptal, Sean spent ten years at Cognizant, where he played various roles, including President of their new Accelerator business division and COO of their Digital Business transformation service line. Sean earned a BS in Computer Science from Cornell University and an MBA from the Wharton School at the University of Pennsylvania.

Bruce Jones

Bruce Jones

Head of Enterprise Sales

As the Head of Global Enterprise Sales for Toptal, Bruce leads a worldwide team responsible for landing new clients and growing revenue in Toptal’s largest accounts. Prior to this role, Bruce was CRO for Civitas Learning where he led a team enabling institutions of higher Ed to leverage data science to increase student success. Prior to Civitas, he spent stints at HPE, IBM, BMC, and Unisys in various sales and sales leadership roles. Bruce graduated from Rhodes College with an accounting degree and holds a CPA certificate.

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.
Toptal Careers

Think you’re a fit? Apply below:


What experience do you have working for a major consulting firm specifically in development of strategic operational frameworks and executive presentations?

How many years of combined business operations and consulting experience do you have?

Do you have experience acting as an internal operational process consultant?

Do you require visa sponsorship, now or in the future?

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Quote author

Agency to create real impact, co-workers who support and challenge you, a work environment designed for high performers, and a powerful mission that seeks to change the future of work; I never thought I would find a company that had them all. I am so glad I made the decision to join Toptal.

Kimberly Hall

VP of Revenue Operations