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Whip Around

Fleet inspections and maintenance management software

Overview

Whip Around provides fleet management software for vehicle and asset inspections and maintenance across industries. It operates on a subscription model with features like customizable inspection forms, a mobile app, fault management, preventative maintenance, work orders, cost tracking, and DOT DVIR compliance to digitize workflows. The platform emphasizes an easy-to-use interface and configurable tools that cover inspections, maintenance, fault and cost tracking, and compliance in one system. Its goal is to help fleets run more efficiently, reduce downtime and costs, and stay compliant by digitizing and streamlining inspection and maintenance processes.

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About Whip Around

Simplify's Rating
Why Whip Around is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Data & AnalyticsAutomotive & TransportationEnterprise Software

Company Size

51-200

Company Stage

Series B

Total Funding

$18.9M

Headquarters

Charlotte, NC

Founded

2016

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Simplify's take

What believers are saying

  • Accel-KKR’s March 3, 2026 majority investment funds product development and acquisitions.
  • Advanced Maintenance launched October 6, 2026, expanding wallet, invoices, and shop-floor automation.
  • GetApp’s October 2026 rankings still place Whip Around among top fleet alternatives.

What critics are saying

  • Fleetio, Samsara, and MaintainX outspend Whip Around on broader platform breadth.
  • Accel-KKR’s March 3, 2026 buyout demands growth, M&A, and integration execution immediately.
  • If DVIR workflows commoditize, Whip Around loses its niche and becomes a feature.

What makes Whip Around unique

  • Whip Around owns DVIR-style inspection workflows, not broad telematics distraction.
  • Advanced Maintenance, launched October 6, 2026, links inspections, work orders, and labor.
  • FixedUnlimited pricing removes per-asset friction for mixed fleets and equipment.

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Funding

Total Funding

$18.9M

Below

Industry Average

Funded Over

2 Rounds

Series B funding is typically for startups that have proven their business model and need more funding to expand rapidly—often by entering new markets or adding more products. Investors are usually venture capital firms that specialize in later-stage investments.
Series B Funding Comparison
Below Average

Industry standards

$35M
$30M
$45M
$65M
$100M

Benefits

  • Unlimited Paid Time Off
  • Health Insurance
  • 401(k) Company Match
  • Parental Leave
  • Professional Development Budget

Growth & Insights and Company News

6 month growth

-2%

1 year growth

-3%

2 year growth

-2%
PR Newswire
Oct 6th, 2026
Whip Around launches AI-powered Advanced Maintenance to connect fleet inspections with shop-floor execution

Whip Around, a fleet maintenance and compliance software platform, has launched Advanced Maintenance, expanding its inspection and maintenance capabilities. The new offering connects mobile inspections with preventive maintenance schedules, work orders, and service history. Advanced Maintenance introduces technician scheduling, labor tracking, cost-based approvals, and AI-assisted review into a unified workflow. The platform uses AI to audit inspection photos for missed defects, automate defect handling decisions, and automatically process work order invoices and receipts. The system enables fleets to capture actual labor time and costs alongside parts and service history, providing visibility into total cost of ownership. It connects inspection findings with asset information and maintenance activity, allowing teams to manage issues from assignment through completion without manual entry. Whip Around serves vocational, freight, and passenger transportation fleets, integrating with ELDs, telematics platforms, and other fleet technologies.

Whip Around
Oct 6th, 2026
Advanced Maintenance is here: fleet maintenance software for one connected workflow.

Advanced Maintenance is here: fleet maintenance software for one connected workflow. Most fleet maintenance software looks backward. It records what happened, but it doesn't help you plan what happens next, and that gap costs fleets money: labor no one tracked accurately, approvals that treat a small repair the same as a major one, and hours spent reviewing inspection photos or retyping invoices by hand. It ships as two separate add-ons instead of one bundled tier, so a fleet adds only the depth it actually needs. Shop Ops: run your shop like a shop. Shop Ops brings real shop floor operations into the platform fleets already use for work orders. Technicians clock in and out against a specific job, so labor cost reflects what actually happened, not what someone remembered to log. A board, calendar, and scheduler replace the whiteboard and guesswork most shops rely on to plan the week, and approval rules route by cost, asset, or team, so a small repair doesn't wait behind the same sign off as a major one. Custom fields let a shop capture whatever it already tracks that a standard work order field doesn't cover, and a completed work order can turn into a quote or invoice in one click, ready to send to a vendor or bill back internally. FleetAI: let AI do the busywork. FleetAI takes on the repetitive, error prone admin work that eats a coordinator's day. AI Inspections Pro analyzes every inspection photo for what a rushed check might miss, and a person always confirms a suggestion before it becomes a defect, so nothing gets created automatically. Workflow automation handles the routine routing decisions a team makes every day, with no limit on how many rules can be set up. Document scanning turns a vendor invoice, fuel receipt, or parts receipt into a structured work order or cost record instead of requiring manual entry. For fleets using Wallet, it also reads registrations, licenses, and permits, and sets expiration reminders automatically. Why two add-ons instead of one bundle. A lot of fleet maintenance software bundles every advanced feature into a single, more expensive tier, so a fleet pays for the whole thing just to get the one capability it actually needs. Advanced Maintenance works the opposite way: a fleet with a shop floor problem adds Shop Ops, a fleet with an admin and automation problem adds FleetAI, and a fleet with both adds both. Nobody pays for a stack of features they'll never touch. Who should look at this first? Shop Ops fits fleets already running an in-house or outsourced shop and creating work orders regularly, especially around 25 or more assets, where manual labor tracking and ad hoc scheduling start to break down. FleetAI fits any fleet already running inspections, regardless of whether Maintenance is part of their plan today. The pattern holds across industries. A construction fleet billing repairs back to a job site cares about approval rules and invoicing. A trucking and delivery fleet trying to answer which trucks cost the most to keep on the road leans on labor cost reporting. A waste and recycling fleet running daily routes needs the scheduler to keep route critical trucks moving through the shop. See it on your fleet. Advanced Maintenance is available now as an add-on to Whip Around's fleet maintenance software platform. If your team still tracks labor by hand, plans next week's shop work off a whiteboard, or spends hours a week on inspection review and invoice entry, book a demo to see Shop Ops and FleetAI on your own fleet's data, or start a free trial to try it yourself. Your drivers make local stops, your trucks are smaller than semis, and none of them needs a commercial... If your trucks cross state lines, buying diesel is only half of the IFTA recordkeeping picture. You also... Get its free guide on silent fleet killers. Table of contents.

PR Newswire
Sep 15th, 2026
Whip Around appoints three fleet tech veterans as company eyes $122B market opportunity

Whip Around, a fleet maintenance and compliance platform, has appointed three executives to its leadership team: Mike Gross as President, Toby McGraw as Chief Revenue Officer, and Julie Chapman as Chief Customer Officer. The appointments come as the company pursues growth in the global fleet management software market, projected to reach over $122 billion by 2035. Gross brings over 20 years of B2B supply chain and operational SaaS experience from roles at vSync, HighJump, and TrueCommerce. McGraw previously served as CRO at Beep and EVP at HopSkipDrive, where he helped drive a tenfold revenue increase. Chapman most recently held customer leadership positions at Immersive and Interos. The company plans to accelerate organic growth, expand through innovation and strategic M&A, and develop a broader fleet operations platform.

Whip Around
Jul 13th, 2026
Whip Around recognized as a top Fleet Maintenance solution for 2026.

Whip Around recognized as a top Fleet Maintenance solution for 2026. Managing a fleet means managing a hundred things that can go wrong: a missed inspection, a defect that never became a work order, a part that ran out before anyone noticed. When those gaps add up, the result is unplanned downtime, compliance exposure, and frustrated crews. The right fleet maintenance software closes those gaps before they become problems. Whip Around is proud to share that Whip Around has earned two major recognitions for 2026: a placement on the Capterra Shortlist for Fleet Maintenance and a spot on Software Advice FrontRunners for Fleet Maintenance. These recognitions are based entirely on verified user reviews and platform performance and they reflect what fleet professionals across construction, trucking, landscaping, and more are finding in the field: that Whip Around works. Whip Around earns 2026 Capterra and Software Advice recognition. The Capterra Shortlist highlights the most popular and highly rated software products in a category, based on verified user reviews and engagement data from real buyers. Software Advice FrontRunners identifies top-performing products by usability and customer satisfaction scores - both factors derived from authenticated user input, not paid placement. Whip Around's inclusion in both reports reflects a consistent track record across more than 570 verified user reviews, with an overall rating of 4.8 out of 5 on Capterra. That rating spans fleets of all sizes, from owner-operators running a handful of vehicles to operations teams managing hundreds of assets across multiple sites. Being recognized in both reports in the same year isn't a coincidence, it's the result of a platform built around how fleet maintenance actually works, not how software vendors think it should work. Fleet maintenance software is a digital system that helps organizations schedule, track, and manage the upkeep of vehicles and equipment - replacing paper logs, disconnected spreadsheets, and reactive repair cycles with a centralized, searchable record of every asset's health. The stakes are real. A fleet running on paper relies on someone to catch the defect, write it down, hand it off, and hope it gets entered into a system before the vehicle goes back out. In practice, things fall through. Vehicles go out with unresolved issues. Inspections go undocumented. Maintenance gets deferred until something breaks. Good equipment maintenance software eliminates that chain of handoffs. When inspections, work orders, and parts inventory live in the same platform, the whole maintenance cycle becomes faster, more consistent, and audit-ready. What Whip Around's platform actually does. Whip Around connects the inspection layer to the maintenance layer, something most telematics-only platforms don't do. When a driver completes a pre-trip or post-trip inspection on the Whip Around mobile app, any flagged defect automatically generates a maintenance work order. That work order gets assigned, tracked, and closed in the same system - no clipboard, no phone call, no lost sticky note. Parts used on the job are logged against inventory, so reorder thresholds can be set before stock runs out. The platform covers vehicle maintenance through to full PM scheduling - set triggers by mileage, engine hours, or calendar date - and stores every inspection record in a searchable, exportable cloud database. For fleets subject to DOT safety audits, that audit-ready recordkeeping isn't a nice-to-have. It's the difference between passing and scrambling. CSA scores are also on the line every time a vehicle goes out with an unresolved defect. Whip Around's compliance dashboard gives fleet managers real-time visibility across the entire fleet, so nothing slips through. What its users are saying. Ratings and badges are useful signals, but the most honest measure of any platform is what the people using it say day to day. Here's what verified Whip Around users on Capterra shared: "It has been a game changer, no more need for paperwork to be printed, used by drivers and mechanics, inputted into the system and then stored in a file, everything is digital and can be pulled up in seconds. Tracking the fleet is so more easier and faster, its a great product! I used it at my last job and when I moved to Montana and was hired here, this product was one of the first things I recommended we start using." "Whip around has really helped me in managing fleets, I wish I had this app when i managed a fleet of 150 frac pumps, it would have made life so simple." "My location tests new technology and decides if it should be implemented throughout the company. Whip Around is a product that passed all of our requirements, and I wish we switched to it years ago. No more paper logs!" Across 570+ reviews, the pattern is consistent: fleets that move from paper to Whip Around spend less time on administrative overhead and more time on keeping vehicles road-ready. The portability matters too, one reviewer brought Whip Around from a previous job to a new employer because the results spoke for themselves. Who uses Whip Around? Whip Around is built for any organization that maintains a fleet, which means it serves a wide range of industries with different compliance requirements, asset types, and operational rhythms. Truck and delivery fleet management teams rely on Whip Around for FMCSA-compliant DVIRs and PM scheduling across CDL fleets. Construction operations use it to track heavy equipment inspections, work orders, and parts inventory across jobsites - fleet management software for construction needs to handle more than just road vehicles, and Whip Around does. Landscaping, waste and recycling, oil and gas, and passenger transport fleets use it too, each with their own inspection forms and compliance considerations. If your organization maintains physical assets and needs documented proof that they're being maintained safely, Whip Around is built for that workflow. About the 2026 awards. Capterra is the #1 destination for organizations researching software. The Capterra Shortlist identifies the most popular and highly rated products in a category, based on ratings and review volume from verified users. Products are not paid for placement - the list reflects genuine user engagement. Software Advice FrontRunners uses independent, objective methodology to score products on Usability and Customer Satisfaction. Products in the FrontRunners quadrant represent the top-performing options in a category as rated by real buyers. Both recognitions are powered entirely by the experiences of verified customers - which is what makes them meaningful. Keep your fleet moving in 2026. Being named to both the Capterra Shortlist and Software Advice FrontRunners for fleet maintenance in the same year reflects something straightforward: fleets that use Whip Around find that it works. Less paper. Fewer defects slipping through. Maintenance schedules that actually get followed. Records that hold up under audit. If you're ready to see what that looks like in practice, book a demo and see how Whip Around works for your fleet. An excavator sitting idle on a jobsite isn't just an inconvenience, it's $450 to $760 an... Managing a fleet means managing a hundred things that can go wrong: a missed inspection, a defect that... Get its free guide on silent fleet killers. Table of contents.

Punakaiki Fund
Mar 3rd, 2026
Whip Around Attracts US Private Equity Majority Investment

Whip Around attracts US private equity majority investment. * March 4, 2026 Punakaiki Fund retains stake in nz-founded company. Punakaiki Fund announces that Whip Around, a New Zealand-founded fleet compliance and operations software platform, has been majority acquired by Accel-KKR. Punakaiki Fund first invested in Whip Around in October 2021, and more recently in mid-2025, and is retaining its stake in the company. Noah Hickey continues to lead Whip Around as CEO, with a mandate to accelerate growth. Accel-KKR brings deep experience supporting software businesses through both organic growth and M&A, and Punakaiki Fund looks forward to supporting the company in these ambitions. The transaction is an exit event for the original founders as well as the majority of investors, while Punakaiki Fund will retain its stake and be the largest New Zealand-based investor in Whip Around. The transaction has received approval from the Overseas Investment Office, as required under New Zealand's overseas investment rules. Terms of the transaction are confidential. "Whip Around's product is an integral part of business-as-usual for fleets across the USA, and it delivers strong economic and safety outcomes for clients and drivers. They capture large volumes of important data that is used to further improve outcomes through partners. We backed the company in 2021 as we believed in the team's ability to build something of genuine global scale from New Zealand. That conviction has not changed, which is why Punakaiki Fund is staying in." Lance Wiggs, Punakaiki Fund Whip Around was formed around the idea of helping truck drivers quickly and thoroughly perform, and digitally track, required vehicle inspections. The company evolved significantly, and their digital platform now allows fleet owners to increase asset utilisation, lower costs and improve safety outcomes. Whip Around provides the source data for a wide range of fleet requirements and has forged strong industry partnerships to deliver exceptional results for their clients. Read the story in NBR. To invest in more companies like Whip Around read its latest share offer

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