A well-known US-based crowdfunding platform that had been live on Rippling for both US and Canadian payroll — US since early 2026, Canada since March 2025 — with a workforce primarily of salaried exempt employees across a significant number of US states and an Ontario presence. The internal team had a part-time payroll consultant providing up to 10 hours per week but needed deeper Rippling expertise for both jurisdictions. The goal was not full outsourcing but rather structured support for payroll processing and preparation while the team retained oversight and approval authority. thePeopleStack proposed a standalone fixed-price payroll audit and shadow engagement — reviewing active payroll cycles for both US and Canada, identifying process gaps and optimization opportunities — as a no-obligation precursor to a potential ongoing managed payroll arrangement. An NDA was executed to facilitate sharing of configuration details.

A US-based online reviews and reputation management platform that recently signed with Rippling after four-plus years on Paylocity, which served as both global HRIS and US payroll system. Migration scope covered approximately 1,000 global employee records (US, India, Philippines, Australia, UK) for document transfer — contracts, NDAs, policies, offer letters, compensation records, pay stubs, and terminated employee records — plus payroll history for 300–400 US employees. Rippling referred thePeopleStack directly as the third-party data migration vendor. thePeopleStack proposed a 10–30 hour discovery phase to assess Paylocity data quality, storage format, and field mapping before committing to full migration pricing — with October 1 as the go-live target and procurement timeline a key risk factor. A full-service extraction approach (thePeopleStack accessing Paylocity directly) and a client-repository approach were both scoped.

A Toronto-based accounting software company with ~300 employees across Canada, the US, the Netherlands, Mexico, and a small EOR population, transitioning from BambooHR — which the seven-person HR team found overly opinionated and dependent on manual intervention for anything beyond basic functions. The company had signed a $30,000 managed implementation contract with Rippling and was seeking a client-side consultant to act as hands-on project manager and configuration resource alongside Rippling's IM team. thePeopleStack was engaged on a monthly retainer model to manage the rollout prioritizing Canada and US payroll for a January 2027 first-check-date go-live, with ATS migration from Gem to Rippling Recruiting and phased global payroll to follow. The HR team had previously experienced a painful self-managed ATS migration and specifically wanted HR-background consultants who knew both the platform and the people operations domain.

A Chicago-based impact investment firm that had been live on Rippling for six months after migrating from Dayforce, with payroll operations across five states running semi-monthly for a mix of salaried and hourly employees. A single internal administrator was carrying the full payroll load — processing, state filings, benefits carrier feeds, and 401k coordination — with Rippling's HR add-on providing compliance reminders but no hands-on execution support. thePeopleStack proposed a two-phase model: a fixed-fee shadowing engagement to observe one to two payroll cycles and validate scope before committing to a retainer, followed by either core managed payroll or full-service HR and payroll support including QLE processing, open enrollment, Fidelity 401k coordination, and 1099 contractor payroll. A Performance Management module migration from Culture Amp was also scoped for Q4.

A US-based property management company engaging thePeopleStack for a full Rippling implementation following a signed MSA and SOW executed in July 2026. The engagement involved multiple stakeholder groups — internal HR/operations, a fractional HR firm, and a benefits broker — coordinated alongside Rippling's dedicated implementation manager. thePeopleStack's consultant (Lyndsi) was designated as the client-side project manager, responsible for coordinating kickoff scheduling, managing stakeholder communication across four internal contacts, and driving implementation execution throughout the engagement.

A US-based legal discovery and eDiscovery SaaS company initiating a Rippling implementation engagement with thePeopleStack in July 2026, following a formal purchase order process. thePeopleStack was introduced via Rippling's partner referral network and assigned a dedicated consultant (Laura Otto) as the primary implementation lead. Phase 1 focused on ADP-to-Rippling document migration as the discovery gate, establishing access protocols, communication workflows, and laying the foundation for subsequent implementation phases.

A US-based investment management firm implementing Rippling for the first time, engaging thePeopleStack for full platform implementation and HR advisory services. Scope covered HRIS configuration, payroll setup, onboarding and offboarding workflows, and compliance advisory — supported by a dedicated consultant team.

A Canadian SaaS company engaged thePeopleStack under a one-year MSA for Rippling configuration, fractional HR services, and ongoing people operations support. Scope included HRIS setup, performance management, compensation planning, talent acquisition support, employee handbook consulting, and compliance advisory — delivered by a fractional HR consultant embedded with the team.

A Toronto-based technology company engaged thePeopleStack for a full managed Rippling implementation under a one-year MSA. thePeopleStack provided a dedicated implementation manager and account principal to lead the rollout, covering HRIS, payroll, benefits, and onboarding workflows using the Prep-Configure-Review methodology — managing the entire implementation process as the client's primary point of contact from kickoff through go-live stabilization.

A fast-growing US-based fiber optic field services company that scaled from under 10 to 43 hourly employees in a short period, with Rippling implemented early but not kept pace with growth. Key friction points included payroll data inconsistencies, a mobile clock-in approach breaking down in a field environment with significant overtime, underutilization of Rippling's finance module for expense workflows, and zero device provisioning across a workforce using personal devices. thePeopleStack engaged on a 20-hour consulting pool to audit the Rippling instance, fix the top payroll and T&A issues, and build a roadmap covering IT security, HR compliance, and fractional People Ops support.

A US-based managed security services provider engaged thePeopleStack for a Rippling healthcheck that evolved into a focused onboarding workflow buildout. The engagement identified gaps in onboarding configuration and shifted to delivering a structured, automated onboarding process within Rippling — covering role-based task assignment, document workflows, and provisioning automation.

A Chicago-based cybercrime defense and ransomware response firm operating a uniquely complex Rippling environment: three S-Corps owning an LLC, three separate login points, and three distinct payrolls coordinated under one instance. The founders were spending excessive time on sporadic platform management, restarting from scratch on every Rippling support call. thePeopleStack conducted a structured four-domain audit covering entity structure and configuration, payroll and contractor workflow gaps (including 1099s paid outside Rippling), QuickBooks Online integration, IT and IAM configuration, and SOC 2 / Drata compliance evidence flows — followed by a retainer model for dedicated ongoing support.

A Vancouver-based professional services company engaged thePeopleStack under a year-long managed implementation agreement beginning in mid-2025, covering fractional HR, recruiting, and Rippling platform management across multiple entities. Scope evolved over time to include global payroll processing, EOR worker onboarding, Canada payroll processing calls, performance management configuration, recruiting and new hire overview, and custom Rippling solutions development. Delivery was led by a dedicated senior consultant embedded with the client team on a recurring basis.

A US-based digital freight and logistics SaaS company implementing Rippling with particular focus on Recruiting ATS configuration. thePeopleStack configured hiring workflows including interview pipelines, role-specific offer letters, email templates, and background check integration, alongside core HRIS and payroll setup and full onboarding and offboarding automation.

A US-based debt recovery and financial services firm implementing Rippling to replace fragmented HR and payroll tools. thePeopleStack delivered a full Rippling implementation covering HRIS setup, payroll configuration, compliance workflows, and admin training to bring the team to operational independence.

A US-based air quality technology company implementing Rippling for the first time across HRIS, payroll, and benefits administration. thePeopleStack provided implementation support covering platform configuration, benefits setup, and onboarding workflow design to give the company a clean, scalable Rippling foundation.

An early-stage US cybersecurity SaaS company implementing Rippling across HRIS, payroll, and identity and access management. thePeopleStack configured role-based app provisioning bundles, automated onboarding and offboarding workflows, and established foundational IAM governance to support the company's security-first operating model.

A North American animation studio with employees across the US and Canada implementing Rippling across both entities. thePeopleStack provided consultative implementation support covering HRIS setup, US and Canadian payroll configuration, benefits administration, and workforce lifecycle workflows tailored to a creative industry employment model.

A US-based construction and field services company using Rippling for HR and payroll alongside Vista ViewPoint for project accounting and HCSS for field operations. Manual data transfer between the three systems was creating reconciliation overhead and errors. thePeopleStack scoped and designed a custom three-way integration to automate data flow between Rippling, ViewPoint, and HCSS, mapping workforce data to field cost codes and project structures.

A US-based commercial lending company that had self-implemented Rippling over three months, reaching approximately 60% completion before stalling. Payroll was live but GL integration with QuickBooks Desktop Enterprise, onboarding automation, benefits configuration, and overtime controls remained incomplete. thePeopleStack engaged on a low-risk 10-hour initial block to scope and execute the remaining priority items: GL upload configuration, automated onboarding with Checkr background checks, overtime approval rules, and multi-state benefits enrollment.

A California-based AI field operations company with W2 employees, a Canadian EOR worker, and ~30 Pakistan-based contractors on 1099s, running Rippling since August 2025 with significant configuration gaps. The Head of People had back-to-back meetings and zero focus time for administrative tasks. thePeopleStack conducted a healthcheck identifying critical CA compliance risks — missing I-9s, unaddressed meal break rules, unused LMS compliance training — then executed a full remediation project across T&A optimization, onboarding automation, payroll configuration, PTO compliance, IT module activation, Slack integration, and contractor hub setup.

A Canadian cultural institution with a mixed workforce of full-time, hourly, and seasonal employees, operating in Alberta under Employment Standards Act requirements. The organization engaged thePeopleStack for a Rippling healthcheck followed by production of a comprehensive SOP library to reduce reliance on institutional knowledge and support operational continuity. thePeopleStack delivered 10 detailed SOPs covering PTO policy assignment by classification, onboarding workflows for all employee types, promotion and lateral move processes, voluntary and involuntary termination offboarding, ROE processing, and Alberta ESA compliance guidance throughout.

A California-based hospice and palliative care organization running Rippling primarily as a payroll and HRIS platform, with heavy reliance on manual workflows, institutional knowledge, and disconnected systems. The HR team faced elevated operational continuity risk as key payroll responsibilities were transitioning away from a single administrator. thePeopleStack conducted a comprehensive healthcheck across six operational areas — payroll, benefits administration, onboarding/offboarding, reporting, device governance, and system utilization — delivered a prioritized remediation roadmap, and transitioned into an ongoing managed payroll and HR advisory engagement under a one-year MSA.

A Canadian cultural heritage nonprofit organization engaging thePeopleStack for a Rippling payroll healthcheck and configuration support. Scope focused on reviewing existing payroll setup, identifying compliance and configuration gaps, and delivering process documentation to support accurate and repeatable payroll operations within Rippling.

A US-based legal technology company with employees across the US, Canada, and UK, engaging thePeopleStack for managed Rippling implementation support. The company needed a client-side project manager and Rippling expert to navigate the complexity of cross-border payroll setup and act as an advocate alongside Rippling's implementation team throughout the engagement.

A Canada-based HR technology company using Rippling across US and Canadian employee populations, engaging thePeopleStack under a 120-hour consulting block for ongoing HRIS optimization and Time & Attendance configuration support. Work spanned HRIS systems advisory, core platform configuration, T&A template preparation and working sessions, payroll advisory, data cleanup for bonus and termination scenarios, and entity setup meetings. Delivered by a senior Rippling consultant with payroll specialist support.

A Tennessee-based professional services firm engaging thePeopleStack for a full Rippling implementation covering HR configuration, payroll setup, and ongoing HR advisory services. Scope included onboarding and offboarding workflow design, compensation planning, HR compliance advisory, and workflow automation. Engagement structured under a master services agreement executed in June 2026 with services delivered across a fixed-scope SOW.

A sustainability and ESG data platform with ~103 salaried employees across the US, UK, Spain, France, Germany, and Netherlands, seeking to outsource payroll operations due to internal staffing transitions and cost-efficiency concerns. The company operated on Rippling with quarterly commission cycles and historical tax issues in the Netherlands and Puerto Rico requiring explicit exclusion from scope. thePeopleStack assumed full ownership of semi-monthly payroll execution: pre-run readiness checks, gross-to-net validation, payroll schedule maintenance, GL mapping stewardship, and stakeholder communication — with the Netherlands and Puerto Rico tax remediation ring-fenced as a separate future engagement.

A US-based semiconductor IP company with employees in the US and a growing India team, implementing Rippling to manage a complex dual-population workforce. India compensation required precise configuration of statutory components including PF employer contributions, HRA, Gratuity, and flexible benefits plans across multiple compensation structures. thePeopleStack designed a comprehensive onboarding process flow covering pre-start, provisioning, ramp-up, and offboarding phases across US and India populations — including contractor vs. employee routing, IT access provisioning (Synopsys, Cadence, AWS, VPN), India statutory compliance, and Carta equity integration.

A US-based government technology firm that had grown rapidly from 13 to nearly 50 employees and was planning to double headcount within 18 months. The company was using Rippling at a surface level only — basic HRIS, ATS, and device management — without leveraging automation, calendar integrations, or approval workflows. thePeopleStack conducted a structured healthcheck across HR, IT, and operations stakeholder groups, identified configuration gaps and missed automation opportunities, and delivered a prioritized remediation roadmap covering PTO sync, onboarding workflows, LMS activation, and a future payroll migration plan.

A Canadian B2B SaaS startup with employees in Ontario and Quebec, and contractors in Australia and Slovakia, implementing Rippling from scratch with a tight payroll deadline. thePeopleStack ran daily working sessions to configure payroll, set up ESA-compliant sick leave and time-off policies, and research international contractor classification risk across two jurisdictions. When founders in Australia and Slovakia were identified as potential misclassification risks, thePeopleStack delivered a compliance risk snapshot and configured Rippling's Contractor Hub as an interim solution.

A Texas-based defense technology company whose Rippling implementation had stalled due to internal HR leadership turnover, incomplete benefits configuration, and critical data gaps — including missing employee SSNs and benefit enrollment errors showing zero deductions. An original HR contact had departed with no meaningful handover, leaving a replacement with two days of orientation and no access to benefits or 401(k) data. thePeopleStack was engaged to audit the existing build, remediate benefits configuration errors (including a misfired flex spend setup), reconstruct the census, and restore implementation momentum ahead of a revised go-live.

A Canadian healthcare company with 335 employees across five legal entities — three Canadian with semi-monthly payroll and two US entities including one with union hourly employees — migrating from ADP. The three-person HR team was managing a simultaneous 40% headcount divestiture while executing a full Rippling implementation, creating extreme bandwidth constraints. Blockers included KYC document mismatches, executive-reversed policy changes, and Rippling's Canadian benefits module limitations for multi-tiered plans. thePeopleStack provided 120 hours of implementation support covering payroll configuration, T&A setup with physical time clocks, ESA-compliant Ontario and Quebec policies, and census data preparation.

A US-based industrial distribution company with offices across Missouri, Kansas, Tennessee, and Illinois, migrating from Paylocity to Rippling with a January 15 first-payroll target. The company engaged thePeopleStack for a two-phase delivery: a structured discovery and planning phase covering four stakeholder groups (HR, IT, Finance, Payroll & Benefits), followed by implementation support. thePeopleStack acted as the client's advocate alongside Rippling's implementation team, running current-state process mapping, data hygiene preparation, and operational ownership design ahead of go-live.

A fast-growing US-based fiber optic telecommunications company that adopted Rippling in 2025 but lacked the bandwidth to fully optimize the platform during rapid market expansion. Manual onboarding workflows — offer letters, NDAs, background checks — were routed through Outlook, Power Automate, and Excel rather than natively in Rippling. thePeopleStack was engaged to replace the existing ATS (JazzHR), consolidate the full hire-to-exit lifecycle into Rippling, and build custom JavaScript-based workflow automation using Rippling Functions to replicate complex role-based provisioning logic.

A Canadian-owned holding company operating out of the Bay Area with a global workforce including ~22–25 Canada-based employees, a secondary 3-person Canadian entity, and contractors in Mexico and the Philippines. The company's payroll lead was departing during implementation, creating an urgent need for a senior subject matter expert to manage the Rippling go-live. thePeopleStack confirmed a September 15 go-live target, managed Canadian regional payroll complexity across BC, Ontario, and Alberta, navigated SunLife benefits integration considerations, and included equity grant administration in scope.

A well-known online crowdfunding platform using Rippling for both US and Canadian payroll, with a workforce primarily of salaried exempt employees across a significant number of US states and an Ontario presence. The internal team had a part-time payroll consultant but was seeking deeper expertise in both jurisdictions. thePeopleStack proposed a fixed-fee payroll audit and shadow phase — reviewing current payroll cycles for both countries, identifying gaps and optimization opportunities — as a no-obligation precursor to a potential managed payroll engagement.

A US-based customer experience SaaS company with ~1,000 global employees and ~300–400 US employees on payroll, transitioning from Paylocity — their global HRIS for four-plus years — to Rippling. Migration scope included employment contracts, NDAs, offer letters, compensation records, pay stubs, and terminated employee records. thePeopleStack proposed a 10–30 hour discovery project to assess data quality in Paylocity and define the migration approach before committing to full execution, with a target Rippling go-live of October 1.

A Toronto-based technology company with ~300 employees across Canada, the US, Netherlands, and Mexico, transitioning from BambooHR — which the internal HR team found overly restrictive and manual-intervention-heavy — to Rippling. A seven-person HR team needed hands-on implementation support and project management to execute the migration without overburdening day-to-day operations. thePeopleStack was engaged on a retainer model to manage the rollout across Canada and the US, replace the existing ATS (Gem) with Rippling Recruiting, and act as the client-side implementation advocate targeting a January 2027 go-live.

A Los Angeles-based AI sales technology company managing multiple acquired business entities — including an SMB with ~40 hourly employees across multiple states, a CA/OH entity, and a 100-person entity with complex multi-state tax setup. thePeopleStack provided ongoing managed Rippling services across all entities: onboarding acquired companies onto Rippling payroll, configuring commission workflows, supporting first payroll runs during critical windows, conducting a payroll risk diagnostic across four environments, and standing up a blended consulting team (senior consultant, payroll specialist, junior support) to manage the acquisition-driven workload cycle.

A US-based energy and crypto mining company with nine legal entities including two Canadian entities, approximately 300 employees, and a July go-live target in Rippling. The client was migrating from Dayforce and facing severe internal bandwidth constraints — the team lacked process knowledge, struggled with data validation, and required structured external project management. thePeopleStack was engaged to pull and compile census data from Dayforce, structure it for Rippling, manage the multi-entity data migration across weekly and biweekly payroll schedules, and provide implementation oversight to keep the project on track.

A US-based digital media and audiobook publisher operating three legal entities with 300+ employees across Maryland, Connecticut, and Virginia, migrating from ADP to Rippling. thePeopleStack managed five concurrent workstreams: resolving ADP–Rippling 401(k) integration gaps including loan over-deduction and match-eligibility date issues; building a full suite of compliant 401(k) automation rules in Rippling; advising on Rippling–NetSuite GL connector architecture; establishing a multi-entity permissions governance framework; and executing a full historical data migration from ADP across all entities.

A sovereign-backed investment fund in the Abu Dhabi Global Market with a globally distributed workforce, operating Rippling in a heavily under-utilized state — functioning as little more than an org chart at engagement start. The UAE payroll module was unavailable, requiring a custom allowances strategy. thePeopleStack deployed a hybrid consulting and development team to rapidly configure HRIS, clean up fragmented permissions, build 3–4 custom Rippling applications for UAE-specific compensation structures, and establish Rippling as the operational system of record for payroll inputs, salary, and accruals — all within a 6–8 week execution window.

A cybersecurity software company migrating from UKG to Rippling across three countries simultaneously — consolidating fragmented payroll vendors and reducing manual admin burden on a lean HR team. Core scope: HRIS, US, UK, and Israel payroll, benefits administration including COBRA and ACA, and data migration from UKG. Add-ons include Time & Attendance with Israel-specific configuration, NetSuite GL integration, Sparkhire ATS migration, Performance Management, and E-Verify. Israel payroll maturity was assessed with the Rippling product team before commitment.

A California-based environmental nonprofit using Rippling for workforce time tracking and Sage Intacct as the financial system of record, with 500+ active project and job codes. Manual Excel-based reconciliation was error-prone and time-consuming. thePeopleStack built a production-grade three-way connector: Sage to Rippling job code sync, Rippling to Sage employee master sync, and Rippling to Sage approved timesheet import for automated T&M invoicing — with California OT and DT bucketing and a full audit trail.

A Canadian technology consultancy implementing Rippling Payroll for the first time, with a simultaneous integration to Harvest for automated time and billing workflows. thePeopleStack configured payroll schedules, earnings codes, deductions, and CRA remittance settings, then built the Rippling–Harvest connector to automate data flow between time tracking and payroll processing.

A US-based telemedicine startup requiring a phased Rippling buildout across three waves: core HRIS, contractor time tracking, HIPAA compliance training via LMS, and device management tracking, followed by full payroll migration from an external provider. Scope included onboarding and offboarding template configuration, role-based access permissions, spend management, and policy document centralization.

A global technology company that had self-implemented Rippling but whose configuration didn't reflect actual HR workflows. A lean HR team needed a trusted partner fluent in HR, IT, and systems — to bridge the gap between HR strategy and system execution. thePeopleStack delivered a consulting retainer to optimize the existing build, translate manual workflows into Rippling-native processes, and advise on future payroll and Time & Attendance module adoption for a primarily Israel-based workforce with international contractors.

An Ontario-based manufacturer with two plants and a predominantly hourly workforce subject to Ontario Employment Standards Act requirements. One plant was live on Rippling Payroll and Time & Attendance including physical time clocks; the second was pending migration. thePeopleStack performed a focused ESA compliance audit covering overtime thresholds, statutory holiday pay, vacation accruals, and time rounding — with the goal of de-risking the second-plant rollout.

A US-based charter aviation company with FAA-regulated workflows and constrained internal HR bandwidth. An initial 30-hour advisory engagement expanded across three phases as scope matured — covering permissions architecture rebuild, payroll history upload, ATS configuration, PTO and benefits, and 401(k) automation. A senior consultant overlay was added for payroll architecture validation and aviation-sensitive compliance workflow design.

A Montreal-based private equity firm managing ~$15B AUM with 120 employees across Montreal, Toronto, and New York. The internal payroll operator went on unexpected leave, creating an urgent need for immediate outsourced payroll coverage — including year-end T4, RL-1, and W-2 processing. thePeopleStack assumed full payroll ownership in Rippling and engaged a Quebec payroll specialist subcontractor for RL-1 and QPP/QPIP accuracy across 80 Quebec employees.

A high-growth cybersecurity SaaS company with a lean three-person HR team supporting 220+ employees across the US, UK, and multiple EMEA countries — including EOR workers. The team discovered thePeopleStack via LLM search after needing support for global payroll complexity and UK pension and HMRC requirements. Engagement began with a fixed-fee healthcheck to surface quick wins, then moved into a managed payroll advisory model with tiered SLA pricing.

A US-based industrial services firm migrating from Gusto, QuickBooks, and TSheets to Rippling. Complex union payroll logic, work-order-aligned time capture, and a mobile field workforce required purpose-built configuration. thePeopleStack co-led delivery with Rippling's implementation team, acting as the client's project manager and translation layer — converting operational reality into Rippling-native workflows, including union dues automation and time-to-work-order mapping.

A modern user research SaaS platform with ~100 employees and contractors distributed across 15+ countries. Roughly half US-based, with the remainder across the UK and EMEA — including EOR workers on Oyster and global contractors previously paid via Deel. Despite having purchased Rippling, the company had no in-house implementation expertise. thePeopleStack delivered a three-phase engagement covering core HRIS, US and UK payroll, global contractor migration, US benefits open enrollment, identity and access management, and a custom-built Oyster-to-Rippling PTO and Google Calendar connector with no off-the-shelf equivalent.