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Enterprise Sales Executive, Banking, Financial Services and Insurance

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Remote from
Canada
Salary
Undisclosed
Department
Sales
Employment
Full Time
Experience
Director
Published
Apply before
24 Nov 2026
Listing views
27
Application actions
1
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AI Summary

The role, at a glance.

Toptal is seeking an enterprise sales executive to build and grow a Banking, Financial Services, and Insurance client portfolio in Canada. The role owns the full sales cycle, from territory planning and prospecting through solution design, complex negotiations, and closing managed-services engagements. Success depends on consultative selling to senior enterprise stakeholders, including procurement, legal, and C-suite decision-makers. The position is remote but field-oriented, with client meetings and periodic travel of up to 25%. It requires strong collaboration with SDRs, pre-sales specialists, delivery teams, and client partners.

Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

Job Complexity

5/5
EasyHard

Pace & Pressure

5/5
RelaxedFast-paced

Autonomy Level

5/5
GuidedFull ownership

Communication Load

5/5
IndependentCollaborative
AI insightThis is a high-pressure enterprise hunter role requiring independent territory creation, complex multi-stakeholder sales pursuits, and credibility with large BFSI organizations. The sales targets, sophisticated service agreements, and need to build a book of business from scratch make it highly demanding.

Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job median (per year)Market rate
$180,000
US market range (per year)$140k–$240k
AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. No employer salary was disclosed. The figures are estimated annual USD base-pay market ranges for a senior enterprise sales executive selling managed technology or consulting services in Canada; variable compensation, commissions, and equity may materially increase total earnings.

Core skills

Skills and capabilities most closely associated with this opportunity.

Sample interview questions
How would you build a new BFSI territory from scratch during your first 90 days?

I would segment the market by strategic fit, buying potential, and urgency, then create account plans for priority organizations. I would map executive and functional stakeholders, use targeted multi-channel outreach, and partner with SDRs and pre-sales teams to convert discovery into qualified pursuits. I would track pipeline coverage, conversion rates, and next steps weekly to refine the plan quickly.

Describe how you sell a complex managed-services solution to an enterprise financial-services client.

I begin with discovery focused on business outcomes, constraints, governance requirements, and the client’s delivery model. I translate the solution into a tailored value case that connects specialist capabilities to measurable strategic priorities, while involving delivery and technical experts early. I maintain alignment across sponsors, users, procurement, legal, and finance through a documented mutual action plan.

How do you establish credibility with C-suite stakeholders in a regulated industry?

I prepare thoroughly on the organization’s strategy, market pressures, technology priorities, and risk environment before engaging. In conversations, I lead with relevant business hypotheses and listen carefully instead of immediately presenting a solution. I earn trust by being precise about capabilities, risks, delivery assumptions, and the measurable outcomes we can jointly pursue.

What is your approach to negotiating a complex services agreement with procurement and legal teams?

I align internal stakeholders on commercial guardrails and delivery commitments before formal negotiation begins. I seek to understand the other party’s priorities early, separate critical risks from lower-impact terms, and keep executive sponsors informed when trade-offs affect business value. My goal is a clear agreement that protects both parties and enables a strong long-term relationship.

How would you manage a sales process in which an initial transactional engagement could grow into a strategic account?

I would deliver a focused initial engagement that addresses an immediate need while identifying adjacent strategic opportunities through regular value reviews. After demonstrating results, I would expand stakeholder coverage, build executive sponsorship, and develop a longer-term account roadmap with the client partner. This approach preserves speed in the initial sale while creating a credible path to broader enterprise adoption.

This analysis is generated from the job description. Salary estimates, role characteristics and sample answers are guidance, not employer-provided facts.
Opportunity details

About this role.

About Toptal

Toptal is a global network of top talent in business, design, and technology that enables companies to scale their teams, on-demand. With $200+ million in annual revenue and team members based around the globe, Toptal is the world’s largest fully remote workforce.

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.

Job Summary:

As an Enterprise Sales Executive on our Banking, Financial Services, and Insurance (BFSI) team, you will build a portfolio of clients by prospecting, pitching, negotiating, and closing new accounts. In this role, you will identify, develop, and close opportunities with enterprise clients by helping them solve complex business challenges across a broad range of capabilities, including technology, marketing, and management consulting. You will develop tailored solutions that help clients accelerate strategic initiatives and achieve measurable business outcomes. This role is designed for true hunters who thrive in a high-performance, client-facing environment. It is ideal for individuals who are passionate about building a territory from the ground up, forging executive relationships, and creating long-term client value.

This is a remote position. We do not offer visa sponsorship or assistance. Resumes and communication must be submitted in English.

Responsibilities:

The following information is intended to describe the general nature and level of work being performed. It is not intended to be an exhaustive list of all duties, responsibilities, or required skills.

You will be responsible for building a targeted portfolio of accounts from scratch – identifying, prioritizing, and developing your own book of business rather than inheriting an existing one. Once you have signed net new customers, you will partner with Client Partners to deepen and expand those strategic relationships over time. Net new accounts typically involve mid-level stakeholders across one or two business units and call for a disciplined, transactional approach, matching skills to immediate needs with speed and precision. As relationships mature, accounts become more complex, with deeper engagement across multiple business units and senior executive relationships. These accounts demand a highly consultative, strategic approach that includes navigating cross-functional priorities, aligning to evolving client business objectives, and demonstrating credibility at the C-suite level. Success will require the ability to adapt your engagement style to the maturity and complexity of each account, while consistently driving value and long-term growth.

  • Working closely with our Sales Development Representatives (SDRs), you will prospect, pitch, negotiate, and close new opportunities while also expanding existing relationships.
  • You’ll operate in a highly collaborative, fast-paced environment, working alongside pre-sales experts and delivery teams to craft compelling, tailored solutions for each client.
  • Your initial portfolio will scale toward an annualized gross sales target of $1M in your first year, with expectations to grow into a $5M book by years 2–3, aligning with our broader portfolio strategies.

We are seeking scrappy, bold, client-obsessed professionals who are energized by face-to-face interaction, inspired by client success, and motivated to close high-impact deals. This is not a “work from your home office” role. We’re looking for professionals who are ready to get in the field, build lasting relationships, and lead with purpose.

In the first week, expect to:

  • Onboard with Toptal, learning the core of our model, our value proposition, and our deep capabilities.
  • Familiarize yourself with the tools and resources needed to be successful.
  • Dive into our sales methods, our selling processes, and playbooks.
  • Become familiar with our contracting and legal methodologies, templates, tools, and processes.

In the first month, expect to:

  • Work with your Portfolio Leader to establish a portfolio strategy and build account plans.
  • Begin to meet with clients, articulate Toptal’s capabilities, and identify where we can help organizations in your territory plan.
  • Meet key Toptal stakeholders who will support your success and the success of the overall team.
  • Learn about the Industry Go-To-Market Strategy, our key sales plays, and our client engagement model.
  • Begin prospecting and actively engaging target accounts within your portfolio.
  • Meet with Sales Development Representatives and Client Partners and cross-functional team members to align on joint account strategies.
  • Collaborate with Pre-Sales Solutions and Delivery teams to understand how we design engagements.

In the first three months, expect to:

  • Conduct research and outreach through multiple channels to uncover new business opportunities within your accounts and drive sales pursuits with cross-functional Toptal teams.
  • Exercise discretion and independent judgment in the negotiation of contracts, work collaboratively with clients, and help them engage Toptal’s engineering, design, and business specialists.
  • Provide consultation or advice to management on policies and procedures.
  • Provide advice and support for the planning of long term or short term business objectives or initiatives.

In the first six months, expect to:

  • Have an initial base of active clients, while continuing to build your overall portfolio.
  • Develop a network of client relationships and build a foundation of advocates and sponsors to expand Toptal’s partnership with existing accounts in alignment with your portfolio strategy.

In the first year, expect to:

  • Have built a list of incredible client accounts, advising them on how to utilize our talent network to build world-class distributed teams and increase efficiency.
  • Begin to mentor new members of the team, teaching them about Toptal, our model, and how to successfully grow their territory.
  • Continue to expand your portfolio of accounts, accelerate growth in your region, and use the full suite of capabilities that Toptal has to offer.

Qualifications and Job Requirements:

  • Bachelor’s degree is required.
  • Extensive experience in engaging and selling Consulting or Managed Services solutions, particularly within Financial Services or Professional Services organizations.
  • Proven track record in full-cycle sales of large, complex, multi-phase, managed technology projects to enterprise clients with $2B+ in annual revenue.
  • A well-rounded understanding of emerging technologies and ability to have an informed discussion about software delivery and development concepts with prospective clients.
  • Ability to build and execute territory plans that lead to consistent portfolio growth and a healthy pipeline.
  • Proven success in prospecting, running virtual sales calls, and leading sales pursuits backed by a multidisciplinary team.
  • Experience negotiating complex service agreements with procurement and legal departments within enterprise accounts.
  • Regular or periodic travel to meet and engage with Toptal clients and customers both inside and outside of your geographic location (25% or less).
  • Outstanding written and verbal communication skills.
  • Ability to work in a fast-paced, rapidly growing company and handle a wide variety of challenges, deadlines, and a diverse array of contacts.
  • 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.

Compensation

Additional Information

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