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Account Executive (US / Canada)

Weekday AI

Canada · On-site Full-time Senior ₹18000k – ₹24000k/yr 6d ago

About the role

Overview

  • Client: Weekday's client
  • Salary range: Rs 18,000,000 – Rs 24,000,000 (ie INR 180 – 240 LPA)
  • Minimum Experience: 4 years
  • Location: USA, Canada
  • Job Type: Full-time

About the Role

You will play a key role in managing and closing high ACV enterprise accounts (valued at $75k and above), developing the enterprise sales strategy across North America, and collaborating closely with the founders and executive team. This position is ideal for a driven and entrepreneurial professional eager to expand a proven sales approach, penetrate enterprise-level clients, and make a lasting impact within a dynamic, early-stage startup environment.

Key Responsibilities

  • Manage and close high-value ACV accounts ($75k+) sourced from a robust pipeline.
  • Establish and lead the enterprise sales process in North America, setting benchmarks for mid-six-figure deals.
  • Collaborate directly with founders and leadership across Customer Success, Product, Engineering, Growth, and Marketing.
  • Attend finance-focused events to network and generate new business opportunities.
  • Guide qualified prospects through the sales cycle from initial engagement to closing.
  • Conduct impactful discovery meetings and product demos, often customized with input from Engineering and Customer Success teams.
  • Manage complex pilot programs with meticulous follow-up, coordinating efforts between internal teams and prospective clients.
  • Negotiate and finalize contracts by convincingly demonstrating our value relative to legacy competitors.
  • Ensure a seamless go-live experience in partnership with Engineering and Solutions teams.
  • Proactively generate a portion of your own leads.
  • Maintain disciplined pipeline management and repeatable processes using CRM tools.
  • Advocate for customer feedback to influence Product development and Go-To-Market strategies.
  • Recruit and expand the North American Account Executive team over time.

Qualifications

  • Minimum of 4 years’ experience selling B2B SaaS solutions to US-based customers.
  • Demonstrated success selling to Mid-Market and Enterprise clients, closing deals with ACVs of $75k+, preferably $100k+.
  • At least 2 years’ experience targeting Finance personas.
  • Proven ability to build, lead, and inspire a high-performing sales team.
  • Experience as one of the initial Account Executives at a startup; comfortable operating in a fast-moving, early-stage environment.
  • Consistent track record of exceeding sales quotas.
  • Strong entrepreneurial drive and resilience; able to thrive amidst the uncertainties inherent to early-stage companies.
  • Excellent project management skills and a proactive approach, essential due to long sales cycles and pilot‑heavy deal structures.
  • Deep understanding of sales methodologies, particularly MEDDPICC.
  • Willingness to begin work at 7:30 AM ET.

Required Skills

  • B2B SaaS Sales
  • Enterprise Sales
  • Mid-Market Sales
  • Finance Persona Sales
  • Pipeline Management
  • Discovery
  • Demos
  • Pilot Management
  • Negotiation
  • Closing
  • CRM
  • Project Management
  • MEDDPICC
  • Team Building
  • Entrepreneurial Mindset

Benefits & Perks

  • Exceptional growth potential, advancing from zero churn to multi-six-figure deals, supported by strong inbound demand.
  • Significant responsibility and influence, working closely with the founders to build the sales motion.
  • Clear opportunities for leadership roles and career progression as the company scales.
  • Minimal bureaucracy, fast-paced autonomy, and the chance to shape foundational sales playbooks.
  • All expenses related to attending finance‑industry events will be covered by the company.

Skills

  • SaaS Sales
  • Enterprise Sales
  • B2B Sales

Requirements

  • Minimum of 4 years’ experience selling B2B SaaS solutions to US-based customers.
  • Demonstrated success selling to Mid-Market and Enterprise clients, closing deals with ACVs of $75k+, preferably $100k+.
  • At least 2 years’ experience targeting Finance personas.
  • Proven ability to build, lead, and inspire a high-performing sales team.
  • Experience as one of the initial Account Executives at a startup; comfortable operating in a fast-moving, early-stage environment.
  • Consistent track record of exceeding sales quotas.
  • Strong entrepreneurial drive and resilience.
  • Excellent project management skills and a proactive approach.
  • Deep understanding of sales methodologies, particularly MEDDPICC.
  • Willingness to begin work at 7:30 AM ET.

Responsibilities

  • Manage and close high-value ACV accounts ($75k+).
  • Establish and lead the enterprise sales process in North America.
  • Collaborate directly with founders and leadership across Customer Success, Product, Engineering, Growth, and Marketing.
  • Attend finance-focused events to network and generate new business opportunities.
  • Guide qualified prospects through the sales cycle from initial engagement to closing.
  • Conduct impactful discovery meetings and product demos.
  • Manage complex pilot programs with meticulous follow-up.
  • Negotiate and finalize contracts by convincingly demonstrating our value relative to legacy competitors.
  • Ensure a seamless go-live experience in partnership with Engineering and Solutions teams.
  • Proactively generate a portion of your own leads.
  • Maintain disciplined pipeline management and repeatable processes using CRM tools.
  • Advocate for customer feedback to influence Product development and Go-To-Market strategies.
  • Recruit and expand the North American Account Executive team over time.

Benefits

All expenses related to attending finance-industry events will be covered by the company.

Skills

B2B SaaS SalesB2B SalesCRMClosingDiscoveryDemosEnterprise SalesFinance Persona SalesMEDDPICCMid-Market SalesNegotiationPilot ManagementPipeline ManagementProject ManagementSaaS SalesTeam Building

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