Manager leading Sun Life’s Prospr service - to - sales teams across insurance and wealth support. Coaching employees, improving operations and identifying client - focused sales opportunities.
About the role
- Enterprise Sales Director selling Sierra’s AI customer-experience platform to Canadian businesses. Managing enterprise relationships, complex six- and seven-figure deals, negotiations, and revenue growth.
Responsibilities
- 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 for key customers and exceed their expectations
- Lead negotiations with existing and prospective customers, 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 for enterprise customers
- 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, personalized outreach, call summarization, pipeline forecasting, and deal execution
- Continuously adopt and experiment with new tools to automate low-value tasks and focus on customer relationships
Requirements
- 6–8 years of experience in an enterprise customer-facing sales role identifying and closing large accounts
- 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 of 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
- 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 to keep you energized
- Discretionary benefit stipend giving people the ability to spend where it matters most
- Free alphorn lessons
- Eligible full-time employees can participate in Sierra's equity plans
Job title
Job type
Experience level
Salary
Degree requirement
No Education Requirement
Location requirements
Report this job
Found something wrong with the page? Please let us know by submitting a report below.
ADP Sales Manager coaching Sun Life’s early - career insurance and wealth advisors. Driving sales productivity, readiness, progression, and continuous improvement.
Field Sales Executive selling Shred - it document destruction services across Vancouver. Building pipelines, managing sales cycles, closing orders, and growing customer relationships for WM Canada.
Freelance sales trainer coaching DACH SaaS and AI teams on discovery, full - cycle selling, and revenue performance. Delivering practical group workshops and 1:1 training mandates.
Vertriebs - Setter qualifiziert täglich warme Leads und terminiert Verkaufsgespräche. FounderBlocks unterstützt Gründer beim Aufbau digitaler Startups und Produkte.
Représentant(e) des ventes pour cVert, entreprise québécoise de traitement de pelouse résidentielle. Répondre aux demandes, proposer des solutions et conclure des ventes à distance.
Senior Sales Executive guiding founders through consultative Growth Discovery at Pilothouse, an ecommerce growth agency. Closing partnerships and improving sales systems with AI and automation.
Sales and service assistant supporting Sun Life’s group benefits business development and client retention. Coordinating inquiries, reports, renewals, correspondence, and administrative operations.
Pharmaceutical sales representative promoting dermatology products to healthcare professionals for Inizio Engage, a healthcare engagement partner. Managing territory strategy, customer relationships, and medical education.
ERP sales representative managing full - cycle B2B sales for Netsuite and Acumatica services and software. Building pipelines, closing complex deals, and growing North American client partnerships.