Enterprise Sales Director, Financial Services

About us

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor and Clay Bavor . Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

About the Financial Services team

Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.

Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.

Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.

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.

What you'll bring

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

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

Strong communication skills: Exceptional verbal and written communication abilities.

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

Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.

Even better...

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

Our values