Head of Global Sales, Loadsmart
$225-275k
+ Incentive bonus and you will also receive stock options
More information about location
Digital freight company for B2B trucking
Be an early applicant
Digital freight company for B2B trucking
201-500 employees
Be an early applicant
$225-275k
+ Incentive bonus and you will also receive stock options
More information about location
201-500 employees
Company mission
To provide transportation services and technology to reduce freight spend, increase service levels and impact team's productivity.
Role
Who you are
- 12+ years of B2B enterprise SaaS sales experience, with a proven track record as a VP/SVP scaling ARR from mid-stage growth through major liquidity events or acquisitions
- Experience presenting to boards of directors, investors, and executive committees on commercial strategy, GTM investment, and revenue forecasts
- Proven expertise architecting global sales motions across complex, multi-product enterprise SaaS portfolios
- Demonstrated experience structuring multi-million-dollar enterprise contracts and strategic partnerships that drive long-term valuation and enterprise value
- Battle-tested experience navigating market shifts, failed playbooks, or GTM missteps, with the ability to spot execution risks early
- Demonstrated high agency and autonomy, with the ability to independently diagnose problems and execute solutions without waiting for direction
- Player-coach mentality with the willingness to operate without mid-management layers, managing flat teams with direct line-of-sight into rep execution
- Must be based in or willing to relocate to Chicago, IL for on-site collaboration
What the job involves
- We are looking for a high-agency, hands-on Head of Global Sales to join our team!
- We are seeking an experienced, battle-tested sales leader who thrives in a flat structure, rolls up their sleeves to manage pipeline discipline, and uses data to drive strategic GTM decisions
- Reporting directly to the CEO, you will bridge the gap between high-level go-to-market strategy and day-to-day tactical execution
- You will unify our enterprise sales organization, lead senior individual contributors, and proactively identify and fix operational gaps
- This is a very exciting and lucrative opportunity for the right leader
- Unify and lead the enterprise sales organization globally, directly managing Sales leadership and Senior Account Executives in a flat-structure environment
- Partner directly with the CEO and Board of Directors to present quarterly sales forecasts, go-to-market strategies, unit economics, and revenue performance metrics
- Align global sales execution, contract structures, and predictable ACV growth directly with the company’s multi-year valuation and strategic exit milestones
- Lead commercial due diligence and go-to-market integration for multi-product expansion and market entry into new international territories
- Translate raw sales operational data into actionable strategic shifts (verticalization, inbound/outbound mix, unit economics, ACV, and cost of sale)
- Maintain extreme tactical discipline across account pipelines, forecast accuracy, stage progression, and rep performance
- Join key prospective enterprise calls to guide deal strategy, provide real-time coaching, and help close complex multi-stakeholder deals
- Build and drive our enterprise outbound motion, establishing clear performance expectations and accountability
- Proactively identify operational and sales process flaws, designing and executing self-directed initiatives to resolve them
- Drive top-level strategic alignment between Sales, RevOps, Product, Marketing, and Customer Success to maximize net revenue retention and lifetime customer value
Our take
Freight services involve many parties including shippers, dispatchers, drivers, and dock managers. Insurance and safety checks are required for everyone involved, a process that makes the truck shipping process more expensive, time-consuming, and less efficient than it could be.
Loadsmart provides an online portal that handles booking, insurance legislation, and health and safety regulations, all within an integrated platform. This digital integration leads to parties receiving instant and guaranteed shipping, offering full financial coverage in the event of any discrepancies.
The company has raised significant amounts of funding, most recently in a 2022 Series D Round, which saw the company achieve a valuation in excess of $1B. It has used this funding to expand its partnership network and to fuel its acquisitions strategy. In the longer term, the company's focus on organic growth will stand it in good stead as it will allow it to avoid aggressive pricing structures, which would make it difficult to achieve profitability given the razor-thin margins in the freight industry.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-21% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Feb 2022
$200m
SERIES D
Nov 2020
$90m
SERIES C
Total funding: $343.7m
Company benefits
- Parental leave: The primary caregiver is able to take three months of fully paid leave and one additionally month of working half days for a total of four months of leave
- Copany Equity: Ever wanted to have a stake in a company? Upon hire, Loadsmart employees are granted options that vest over a four-year period
- Team Building Events: Enjoy local company sponsored events to meet and network with fellow Loadies: from hackathons to local meetups, we love collaborating while having fun
- 401K wwith Match: We support our employees' retirement goals by offering a per pay period match to our Traditional and Roth 401K plans
- 401K with Match: We support our employees' retirement goals by offering a per pay period match to our Traditional and Roth 401K plans
- Healthcare: We offer competitive medical, dental, and vision coverage for you and your family
- Claim Advocacy with MMA: Expert advocacy and guidance on benefits and claims
- HSA/FSA: You can use pre-tax dollars to pay for healthcare costs for you and your dependents
- DCFSA: We offer DCFSA to help parents reduce their total taxable income when paying for childcare
- LPFSA: On eligible plans, LPFSA helps pay for vision and dental expenses that are not fully covered by your insurance
- Life and AD&D Insurance: Loadsmart provides both Life and Accidental Death and Dismemberment insurance at no cost yo you with the options to increase coverage at your own expense
- Short Term/Long Term Disability Insurance: Loadsmart provides short and log-term disability coverage at no cost to you
- FLexibe PTO?Holiday: Enjoy paid time off without a limit, with manager approval and national holidays of your location
Company HQ
Chicago Loop, Chicago, IL
Leadership
Felipe Capella
(Co-Founder & CEO)Previously Attorney at Inter-American Development Bank for 1 year and Professor of Bankruptcy and Restructuring at Universidade Federal de Santa Catarina for 2 years.
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