Senior Director of People Operations, Loadsmart
$165-195k
+ Eligible for an incentive bonus, stock options, and equity package
Digital freight company for B2B trucking
Be an early applicant
Digital freight company for B2B trucking
201-500 employees
Be an early applicant
$165-195k
+ Eligible for an incentive bonus, stock options, and equity package
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
- 10+ years of HR experience, with at least 3-5 years in a senior HR leadership role (Senior Director HR, Head of HR, or similar), preferably within a tech or freight tech environment
- Demonstrated deep expertise in compensation, including a proven track record of designing and implementing innovative compensation structures, incentive plans, and total rewards strategies. Experience with global compensation practices is a significant plus
- Strong business acumen and financial literacy, with a clear understanding of how HR initiatives impact financial performance and profitability
- Experience operating in an environment focused on cost optimization and driving efficiency
- Proven ability to develop and implement pragmatic HR solutions that address both strategic objectives and operational realities
- Exceptional leadership and team management skills, with experience leading and developing global HR teams
- Excellent communication, interpersonal, and influencing skills, with the ability to build strong relationships across all levels of the organization
- Experience working in a fast-paced, growth-oriented startup environment, dynamic settings where adaptability and hands-on problem-solving are essential
- Bachelor's degree in Human Resources, Business Administration, or a related field. Master's degree or relevant HR certifications (e.g., SPHR, SHRM-SCP, CCP) preferred
What the job involves
- We are seeking a highly experienced and strategic Senior Director of People Operations to lead our global HR function
- Reporting directly to the Chief Financial Officer (CFO), this is a critical leadership role that will partner closely with the executive team to drive our people strategy, ensuring it directly supports our business objectives, particularly our journey towards profitable growth and operational efficiency
- You'll be instrumental in shaping our organizational culture, optimizing our talent, and providing expert guidance across all HR disciplines, with a strong emphasis on compensation
- Act as a trusted advisor to the CFO and executive leadership team, developing and executing HR strategies that align with and advance the company’s overall business goals, with a particular focus on supporting growth, profitability, and cost efficiency from a people perspective
- Develop and implement strategies for talent management, performance management, and employee development that optimize talent investment while fostering growth
- Serve as the primary subject matter expert and thought leader for all compensation matters, including base pay, incentive plan design, and long-term incentives — to attract, retain, and motivate top talent while maintaining cost-effectiveness and internal equity
- Partner with leadership to develop innovative incentive plans that drive desired business outcomes and support our profitability goals
- Drive culture and engagement across all employees, especially considering the unique dynamics of our in-person brokerage team in Chicago, our Brazil-based engineering team, and a significant remote workforce
- Oversee the effective administration of all benefits programs
- Design and clearly communicate career paths and growth opportunities for employees
- Champion a culture of continuous learning and development
- Lead initiatives related to organizational design, workforce planning, and change management to enhance efficiency and productivity
- Ensure HR policies and practices comply with global regulations and support a positive, productive work environment
- Lead, mentor, and develop a high-performing HR team
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 achieving 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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