Enterprise Sales Director Financial Services
Enterprise conversational-AI platform that helps businesses build and operate customer-experience agents across channels.
Maintainer signals as of 9/23/2026
About Sierra
Sierra provides an AI platform for businesses to build, deploy, analyze, and optimize customer-facing agents across chat, SMS, WhatsApp, email, voice, and ChatGPT.
Skills
Candidate Availability
Required and preferred rules are kept separate and reflect the wording in the original posting.
About the Role
You will identify and engage enterprise prospects, build relationships with key decision-makers, and manage complex sales cycles. You will negotiate contracts, develop tailored sales strategies and proposals, collaborate across go-to-market functions, and use AI tools to improve account research, outreach, forecasting, and deal execution.
Requirements
- 6-8 years of experience in an enterprise customer-facing sales role identifying and closing large accounts
- Experience managing a $1M+ quota and 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 enterprise prospecting and lead-generation experience through research, networking, and cold calling
Responsibilities
- Identify and target potential customers through research, networking, and cold calling
- Build relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity
- Build and maintain relationships with key decision-makers and stakeholders
- Lead negotiations, address objections, and close complex deals
- Navigate contracts and agreements with legal and finance stakeholders
- Develop and execute sales strategies to meet or exceed sales targets
- Craft tailored sales presentations and proposals
- Collaborate with marketing, go-to-market, product, technical, and operations functions
- Use AI tools for account research, outreach, call summarization, pipeline forecasting, and deal execution
Benefits
- Flexible unlimited paid time off
- Medical, dental, and vision benefits for employees and their families
- Life insurance and disability benefits
- Retirement plan dependent on country of employment
- Parental leave
- Fertility and family-building benefits through Carrot
- Lunch, snacks, and coffee
- Discretionary benefit stipend
- Free alphorn lessons
- Equity plan participation
