Global Enterprise Sales Leader | Strategy & Growth

Loadsmart; Chicago (IL); On-site; USD 225,000 - 275,000; Full time

Benefits offered by this job

Competitive base salaries

Equity package

Loadie Time Off — PTO and sick days

Medical, Dental, and Vision insurance

401k Match

Job summary

Loadsmart is seeking a high-agency Head of Global Sales to bridge executive strategy and day-to-day execution. You will unify the enterprise sales organization, manage senior contributors, and drive disciplined pipeline management in a flat-structure environment.

You will partner with the CEO and Board to present forecasts, align contracts, and steer multi-product expansion across international markets. Chicago-based, on-site with relocation possible.

Qualifications

• 12+ years of B2B enterprise SaaS sales experience; track record as VP/SVP scaling ARR
• Experience presenting to boards, investors, and exec committees on commercial strategy and forecasts
• Proven expertise architecting global sales motions across multi-product SaaS portfolios
• Experience structuring multi-million-dollar enterprise contracts and strategic partnerships
• Battle-tested in navigating market shifts and GTM missteps with proactive risk spotting
• High agency and autonomy; able to diagnose problems and execute without direction

Responsibilities

• Unify and lead the enterprise sales organization globally; manage Sales leadership and Senior Account Executives
• Partner with CEO and Board to present quarterly forecasts and GTM strategies
• Align global sales execution, contracts, and ACV growth with company valuation milestones
• Lead due diligence and GTM integration for multi-product expansion into new territories
• Translate sales data into strategic shifts (verticals, inbound/outbound mix, cost of sale)
• Maintain discipline over pipelines, forecasts, and rep performance
• Join enterprise calls to guide deal strategy and close complex multi-stakeholder deals
• Drive enterprise outbound motion with clear performance expectations and accountability
• Identify and fix sales process flaws with self-directed initiatives
• Drive alignment between Sales, RevOps, Product, Marketing, and Customer Success to maximize NRR and LTV

Skills

B2B enterprise SaaS sales

Board presentation

Global sales motions

Enterprise contract structuring

Autonomy and initiative

Flat-team leadership

Job description

Loadsmart is seeking a high-agency Head of Global Sales to bridge executive strategy and day-to-day execution. You will unify the enterprise sales organization, manage senior contributors, and drive disciplined pipeline management in a flat-structure environment.

You will partner with the CEO and Board to present forecasts, align contracts, and steer multi-product expansion across international markets. Chicago-based, on-site with relocation possible.