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Weekday AI (YC W21) - remotehey
Weekday AI (YC W21)

Account Executive

canada / Posted
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This role is for one of the Weekday's clients

Salary range: Rs 18000000 - Rs 24000000 (ie INR 180 - 240 LPA)

Min Experience: 4 years

Location: USA, Canada

JobType: full-time

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.

Requirements

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