Sales Leader, Enterprise

Jobgether; United States; Remote; USD 249,000 - 297,000; Full time

Benefits offered by this job

Equity opportunities

Unlimited PTO

Stock options: 10-year exercise window

Equipment & software budget

Education budget

Fully remote work

Professional development

Career progression opportunities

Job summary

Jobgether is seeking a high-impact Enterprise Account Executive leader to drive revenue for the Enterprise segment from a remote Canada base. You will partner with senior peers, lead complex cycles, and build a scalable team that consistently closes strategic multi-million deals.

You will own go-to-market strategy, coach teams, and ensure alignment across Product, Marketing, and Solutions Engineering, while maintaining close involvement in day-to-day deals and pipeline management.

Qualifications

• Led and scaled a SaaS Enterprise Account Executives team in a growth-focused org.
• Experience delivering at least $5M in annual revenue for an enterprise team.
• Proven track record winning complex SaaS deals valued at $1M+ with public companies.
• Recruited, hired, onboarded and developed EAE to independently generate pipeline.
• Strong enterprise sales strategy, forecasting, negotiation and competitive positioning.
• Experience selling multi-product SaaS platforms and replacement opportunities.
• Strategic leadership while staying involved in key deals and daily ops.
• Excellent customer relationships and senior-level engagement ability.
• Deep product/industry expertise and ability to translate to customer value.
• Collaborative cross-functional leadership with Product, Marketing, Solutions Eng.
• Ownership mindset, sound judgment, clear communication and growth mindset.
• Nice to have: experience selling to Talent Acquisition/People leaders.
• Location requirement: based in Canada, comfortable with remote work.

Responsibilities

• Own revenue outcomes for the Enterprise segment and achieve sales targets.
• Partner with senior EAE through team-selling to improve win rates on big opportunities.
• Provide hands-on leadership through complex enterprise sales cycles and close strategic accounts.
• Build, hire and scale a high-caliber Enterprise Account Exec team.
• Coach sales pros to generate their own pipeline and close both tactical and strategic deals.
• Establish and reinforce a strong enterprise sales methodology with continuous learning.
• Build trusted relationships with customers and facilitate peer-level conversations.
• Develop deep portfolio/product knowledge and articulate customer value.
• Drive alignment with Product, Marketing, Solutions Eng, and PS for growth.
• Contribute to go-to-market strategy, sales planning and org development.
• Maintain active involvement in deal strategy, pipeline management and ops.
• Report to Head of AMER Sales and align with senior leadership on priorities.

Job description

Accountabilities

- Own revenue outcomes for the Enterprise segment, ensuring accountability for performance, growth, and achievement of sales targets.

- Partner with senior Enterprise Account Executives through a collaborative team-selling approach to improve win rates on the organization's largest opportunities.

- Provide hands‑on leadership throughout complex enterprise sales cycles, helping teams assess deal risks, navigate competitive replacement opportunities, and close strategic accounts.

- Build, hire, onboard, and scale a high‑caliber team of Enterprise Account Executives in line with market demand and business priorities.

- Coach and develop sales professionals to generate their own pipeline and successfully close both tactical deals and larger strategic opportunities.

- Establish and reinforce a strong enterprise sales methodology, encouraging continuous learning, experimentation, and consistent execution.

- Build trusted relationships with customers and facilitate strategic, peer‑level conversations between senior business leaders.

- Develop deep expertise in the product portfolio and the broader talent acquisition technology market, enabling the team to deliver informed, differentiated customer engagements.

- Drive alignment across Product, Marketing, Solutions Engineering, and Professional Services to strengthen enterprise acquisition and create a repeatable growth engine.

- Contribute significantly to go‑to‑market strategy, sales planning, and the continued development of the enterprise sales organization.

- Maintain an active role in deal strategy, pipeline management, and day‑to‑day sales operations rather than focusing exclusively on reporting and forecasting.

- Report to the Head of AMER Sales and collaborate with senior leadership on segment priorities and long‑term growth.

Requirements:

- Demonstrated experience leading and scaling a team of SaaS Enterprise Account Executives in an organization that has grown beyond $100 million in annual recurring revenue.

- Track record of leading an enterprise sales team delivering at least $5 million in annual revenue.

- Experience helping win complex SaaS deals valued at $1 million or more with publicly traded companies.

- Proven ability to recruit, hire, onboard, and develop Enterprise Account Executives who can independently generate pipeline and close deals ranging from approximately $100,000 to $500,000 or more.

- Strong understanding of enterprise sales strategy and execution, including pipeline development, deal qualification, forecasting, negotiation, and competitive positioning.

- Experience successfully selling complex, multi‑product SaaS platforms and winning competitive replacement or rip‑and‑replace sales opportunities.

- Ability to lead strategically while remaining directly involved in important deals and the daily operations of the sales team.

- Strong customer relationship skills, with the confidence to facilitate senior‑level conversations and build long‑term strategic partnerships.

- Ability to develop deep product and industry expertise and translate complex capabilities into practical customer value.

- Collaborative leadership style, with experience working across Product, Marketing, Solutions Engineering, and Professional Services.

- Strong sense of ownership, sound judgment, and principled decision‑making, combined with clear and thoughtful communication.

- Growth mindset and willingness to learn, experiment, and adapt sales approaches as the product portfolio and market evolve.

- Nice to have: Experience selling to Talent Acquisition and/or People leaders, with an understanding of their priorities, challenges, and purchasing needs.

- Location: Candidates must be based in Canada and comfortable working remotely.

Benefits:

- Competitive compensation package of CA$352,000–CA$418,500 , with a 50/50 base salary and commission split.

- Equity opportunities.

- Unlimited paid time off, with four weeks recommended annually.

- 10‑year exercise window for stock options.

- Generous budget for equipment, software, and office furniture.

- Monthly education budget of $100, with additional learning expenses such as conferences potentially covered with manager approval.

- Fully remote working arrangement.

- Opportunity to lead a high‑impact enterprise sales segment and help shape the growth of a multi‑product SaaS platform.

- Professional development opportunities, with an emphasis on coaching, career progression, and continuous learning.