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Drive My Way

Drive My Way

Private
Cleveland, OhioMobility, Transportation & Logisticshttps://www.drivemyway.com/

Last Round

Series A

Oct 27, 2022

Total Funding Raised

$4.4M

Company Overview

Drive My Way is a transportation and logistics company that operates a personalized recruiting platform matching CDL truck drivers with employers based on professional qualifications and lifestyle preferences.

Sector

Mobility, Transportation & Logistics

Verticals

HR, Freight & Transportation, Logistics Software

Business Model

B2B

Customer Profile

Subscription SaaS, Services & Consulting

AI Layer

Application

Keywords

CDL driver recruitingtrucking marketplacedriver retentiontruck driver jobsCDLrecruiting softwarevertical SaaSowner-operator recruitinglogistics hiringdriver matchingjob boardtrucking headhunterdriver sourcing

Historical Pricing

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Caplight Momentum Score

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Drive My Way Comparables

Compare Drive My Way with similar companies based on industry and business-model similarity.

Drive My Way comparables — related companies by embedding similarity
CompanySimilarityMarket Cap
YouCruit
92%
AllTruckJobs
87%
CDL Job Now
84%

Drive My Way Funding Rounds

Historical fundraising activity

Data table
RoundDateAmount RaisedValuationInvestorsSources
Series AOct 27, 2022

Key People

Founding team and executive leadership

E. Timothy Holzheimer

Chief Financial Officer

Executive Team

Rich Shopmyer

Chief Operating Officer

Executive Team

Drive My Way Investors

Notable investors and investment history

Drive My Way investors
InvestorRounds
JumpStart VenturesSeries A
First AnalysisSeries A
FlashstartsAccelerator
M7 HoldingsSeries A

Market signals

Structured signals derived from secondary market and firmographic data.

  • Mar 2, 2026

    Monthly visitors increased 42% MoM.

  • Jun 1, 2025

    Monthly visitors grew 39% MoM, reaching 26.5K.

Drive My Way Filings

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Drive My Way filings preview — column headings only; records require access
TypeDateAmount OfferedAmount SoldFilingPagesDownload

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Frequently Asked Questions

Common questions about Drive My Way's valuation, stock price, and market status.

Is Drive My Way a public or private company?

Drive My Way is a private company.

What is the current stock price of Drive My Way?

Drive My Way is a private company, so its shares have no public market price. Caplight tracks Drive My Way's secondary market activity and provides MarketPrice™ estimates of its share price to Caplight users.

How much is Drive My Way worth (valuation)?

Valuation information for Drive My Way is not publicly available.

Can I buy Drive My Way stock?

Drive My Way shares may be available on secondary markets subject to transfer restrictions. Caplight facilitates secondary market transactions for accredited investors.

When was Drive My Way's last funding round?

Drive My Way's most recent funding round was Series A on October 27, 2022.

Who are the main investors in Drive My Way?

Key investors in Drive My Way include First Analysis.

Will Drive My Way IPO soon?

No public IPO plans have been announced for Drive My Way.

How can I track Drive My Way secondary market activity?

Caplight tracks bids, offers, and trades in Drive My Way's shares on secondary markets.

Firmographic Details

HeadquartersCleveland, Ohio
Employee Range20
Year Founded2014
Last FundingOct 27, 2022

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