Enterprise Sales Director, Financial Services

About the role

You will own the development and execution of enterprise sales strategies within the financial services sector, driving both new business acquisition and expansion of existing marquee clients. This role requires you to act as a strategic advisor to systemically important banks, insurers, and vertically integrated ecosystems, helping them leverage AI to modernize their customer experiences. You will be responsible for navigating complex enterprise decision-making units and building long-term partnerships based on trust and measurable business outcomes. A core part of this position involves using data and AI tools to identify high-impact opportunities and streamline the deal lifecycle. You will collaborate directly with product and technical teams to ensure our solutions align with the evolving needs of the market. This is a leadership position that demands intensity and craftsmanship in equal measure, as you guide critical deployments that impact billions in economic activity. You will set the standard for customer obsession by anticipating unspoken needs and delivering responses that reinforce our credibility and reliability.

Key facts

What you'll do

Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.

Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.

Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.

Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.

Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.

Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

Analyze pipeline health and forecast accuracy: Use data to identify risks and opportunities within the sales funnel, ensuring predictable revenue generation.

Champion product feedback: Synthesize insights from customer interactions to inform product improvements and positioning adjustments.

Requirements

6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.

Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.

Exceptional verbal and written communication abilities.

Ability to analyze market trends, identify opportunities, and make data-driven decisions.

Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.

Familiarity with the AI landscape, key players, and emerging trends.

Commitment to upholding the values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family in all professional interactions.

Ability to operate effectively in a fast-paced, mission-critical environment where accuracy and empathy are equally important.

Nice to have

Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.

Practical notes

Full-time based in the US

Remote.

Work hours are aligned with business hours in the Americas, requiring availability during standard working hours for collaboration with internal teams and external clients in overlapping time zones.

About Sierra

Sierra is hiring for Enterprise Sales Director, Financial Services. The listing location is US

Remote.

This Enterprise Sales Director, Financial Services opening is posted for US

Remote.