Enterprise Sales Director, Financial Services

Sierra

Enterprise Sales Director growing Sierra’s AI customer-experience platform among Canadian banks, insurers, and financial-services firms. Managing complex enterprise deals, strategic relationships, negotiations, and AI-enabled sales execution.

Posted 8/5/2026full-timeRemote • 🇨🇦 CanadaLead💰 CA$305,000 - CA$370,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in enterprise sales with a proven ability to manage complex deals and exceed revenue targets. Skilled in building relationships with key decision-makers and leveraging AI tools for enhanced sales strategies and execution.

Highest-signal resume keywords

Enterprise Sales ExperienceComplex Deal NegotiationQuota Management Over $1MMarket Trend AnalysisAI Tools Utilization

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Strategy DevelopmentCold CallingRelationship BuildingProposal CreationData-Driven Decision Making

Soft Skills

Exceptional CommunicationNegotiation SkillsCustomer Relationship Management

Tools & Technologies

AI Tools for SalesSales Presentations Software

Industry Keywords

Enterprise CustomersGTM Team Collaboration6- and 7-Figure ACV DealsStakeholder Engagement

About the role

Key responsibilities & impact

Identify and target potential customers through research, networking, and cold calling
Build new relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity
Build and maintain relationships with key decision-makers and stakeholders at the largest customers
Serve as the primary point of contact and exceed customer expectations
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 targets
Create tailored sales presentations and proposals
Collaborate with marketing on sales campaigns and presentations
Work with the broader GTM team and product, technical, and operations organizations
Leverage AI tools across account research, outreach, call summarization, forecasting, and deal execution

Requirements

What you’ll need

6–8 years of experience in an enterprise customer-facing sales role
Experience managing a $1M+ quota
Experience 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 identifying and targeting enterprise clients through research, networking, and cold calling
Familiarity with the AI landscape, key players, and emerging trends is an advantage

Benefits

Comp & perks

Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee
Discretionary benefit stipend
Free alphorn lessons
Eligible full-time employees can participate in Sierra's equity plans
Offers commission