Crossroads Tax Advisors

What Crossroads Tax Advisors does

Crossroads Tax Advisors is a privately held, founder-owned CPA firm founded in 2008 by Chris Cuadros in Greenwood, Indiana, that delivers accounting, tax planning, tax preparation, and remote CFO advisory services exclusively to dental and other private healthcare practices in the United States. The firm operates on a cloud-based technology stack centered on the Canopy client portal, integrated with QuickBooks Online for real-time accounting, Dext for AI-powered receipt capture, Fathom for financial analysis and custom KPI reporting, and Microsoft Teams for client video meetings, enabling remote service delivery from a single Indiana headquarters. Its go-to-market is consultative: prospects enter through website inquiry forms or a Calendly-scheduled discovery call and receive a complimentary CPA Checkup, after which they convert into recurring monthly retainer engagements plus seasonal and project-based tax and advisory work, with pricing quote-based and not publicly disclosed. The team has grown to approximately 13 members, including CPAs, tax and accounting managers, a Director of Business Development, and a Director of Operations, and the firm supplements its services through a referral ecosystem of healthcare-specialized partners covering lending, practice transitions, HR, marketing, legal, and practice management consulting.

Name

Crossroads Tax Advisors

Legal name

Crossroads Tax Advisors

Website

https://crossroadstax.com

Company type

Private

Founded year

2008

Operating status

Operating

Headcount range

1–10 employees

Short description

Crossroads Tax Advisors is a privately held Greenwood, Indiana-based CPA firm founded in 2008 that provides specialized accounting, tax planning, tax preparation, and remote CFO services exclusively to U.S. dental and other private healthcare practices, delivered remotely through a cloud-based technology stack.

Ownership category

akta.pro rank

Product category

Healthcare Practice Accounting & Tax Services

NAICS

Offices of Certified Public Accountants (541211), Accounting, Tax Preparation, Bookkeeping, and Payroll Services (5412), Other Accounting Services (541219)

SIC

Services-Management Consulting Services (8742), Finance Services (6199)

akta.pro primary industry

Financial Reporting & Technical Accounting Advisory (GAAP/IFRS) (BPAHABAF)

akta.pro secondary industries

Transaction Tax Structuring & Deal Advisory (BPAHAOAJ), Trust & Estate Tax Planning & Compliance (FSAEAKAE)

Keywords

• Dental practice accounting
• Healthcare tax services
• Tax planning preparation
• Bookkeeping services
• Remote CFO services

Headquarters

HQ city

Greenwood

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Technology or R&D, Operations, Marketing or Sales

Revenue model

1. Accounting & Bookkeeping Services: Ongoing monthly and quarterly accounting services including data entry, account reconciliations, adjusting journal entries, and financial statement preparation. Serves as the practice's internal accounting department on a recurring basis.
2. Tax Planning & Preparation: Comprehensive tax services including federal and state tax return filing, personal and business taxes, audit services and representation, tax projections, profit planning, and tax minimization strategies. Also includes estate tax planning and tax planning for mergers, acquisitions, and sales.
3. Complimentary CPA Checkup: Free initial evaluation for prospects that examines current practice tax and accounting, reveals improvement opportunities, and demonstrates value prior to conversion. Serves as lead generation for paid services.

Pricing tiers

Go-to-market motion1 record

Distribution channels3 records

Marketing channels5 records

Core offering

Crossroads Tax Advisors provides specialized accounting, tax planning, and tax preparation services exclusively to dental and healthcare practices. The firm operates as a remote, cloud-based outsourced accounting department offering recurring bookkeeping, real-time financial reporting with industry-specific KPIs, year-round tax strategy, audit representation, and Remote CFO Services delivered via an integrated technology stack (Canopy, QuickBooks Online, Dext, Fathom, Microsoft Teams).

Product overview

Crossroads Tax Advisors operates as a specialized accounting and tax services firm for dental and healthcare practices, built on a technology platform centered around Canopy as the core client portal. The integrated software stack includes Quickbooks Online for real-time accounting, Dext for AI-powered receipt management, Fathom for financial analysis, and Microsoft Teams for video consultations. The firm offers complementary CPA checkups as an entry point, followed by ongoing Remote CFO Services, Healthcare Practice Reporting, and comprehensive Tax Planning & Preparation. All services are delivered through cloud-based technology enabling 24/7 real-time connectivity between clients and the accounting team.

Differentiator

Problem solved

Functional benefit

Products and services

• Accounting Services Recurring outsourced bookkeeping and accounting delivered as a remote internal accounting department for dental and healthcare practice owners, including weekly, monthly, and yearly reconciliation and financial statement preparation with healthcare-specialized charts of accounts.
• Tax Planning & Preparation Comprehensive year-round tax services for dental and healthcare practice owners, including federal/state tax return preparation, audit representation, tax projections, profit planning, tax minimization strategies, and estate tax planning for mergers, acquisitions, and sales.
• Remote CFO Services Outsourced CFO advisory for dental and healthcare practices providing strategic financial guidance, goal identification, growth planning, and ongoing decision support delivered remotely via cloud-based technology.
• Healthcare Practice Reporting & KPIs Custom KPI monitoring and benchmarking service for dental and healthcare practices, delivering industry-specific performance indicators and practice-specific reports on a recurring basis.
• Complimentary CPA Checkup Complimentary evaluation of a dental or healthcare practice's current accounting and tax situation that identifies improvement opportunities and serves as the firm's lead generation mechanism into paid engagements.
• Business Software Implementation Implementation, configuration, and ongoing support of an integrated cloud accounting software stack (Canopy, QuickBooks Online, Dext, Fathom, Microsoft Teams) for dental and healthcare practice clients.

Quantifiable outcome

• Free up practice owner time to focus on patient care rather than administrative financial management
• +2 more outcomes

Named customers6 records

Segments2 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration5 records

AI capability5 records

Feature3 records

Partnerships

13 partnerships are on record, tiered core, secondary and minor.

• CanopycoreTechnology or IntegrationCanopy serves as the heartbeat of Crossroads Tax technology platform - a private and secure location for client tax documents and financials. Enables real-time connection with clients for uploading, downloading, and reviewing documents from any device. Replaces risky email transmission of confidential information.
• QuickBooks OnlinecoreTechnology or IntegrationAccounting software providing real-time practice data access for clients, Crossroads CPAs, and other advisors from any device and location. Eliminates manual data entry and fax/email transmission inefficiencies.
• DextcoreTechnology or IntegrationReceipt management technology using AI to photograph, read, categorize, and store receipt data. One-click delivery of organized data to CPA eliminates data entry and manual transmission. Available as phone app or desktop software.
• Microsoft TeamssecondaryTechnology or IntegrationVideo conferencing platform for collaborative online meetings. Crossroads uses for twice-yearly planning and review meetings with clients. Provides more effective communication than phone conferences with human interactive elements.
• FathomsecondaryTechnology or IntegrationFinancial analysis tool that translates QuickBooks data into easy-to-read custom reports for practice performance tracking. Enables monthly cash flow reviews and long-term revenue trend analysis tied to practice goals.
• ProvideminorStrategic or Co-development PartnerTom Muck from Provide discusses the lending process for doctors, including how to pick the right lender, differences between banks, and how Provide supports doctors through the lending process. Crossroads works with Provide as part of comprehensive dental practice advisory team.
• Legacy Practice TransitionsminorStrategic or Co-development PartnerSherry Foster from Legacy Practice Transitions discusses practice transition and acquisition issues in the dental community. Crossroads team member Jason Hite collaborates on addressing practice transition challenges facing dental professionals.
• Bent EricksenminorStrategic or Co-development PartnerRobyn Reis from Bent Ericksen provides HR consulting services for healthcare practices. Discusses HR support for doctors ensuring compliance with employment considerations. Works as part of Crossroads' comprehensive dental practice advisory ecosystem.
• EOS Healthcare MarketingminorStrategic or Co-development PartnerNate Woudstra discusses marketing approaches for healthcare clients, current marketing industry topics, and how EOS works with doctors' advisory teams to bring added value. Part of Crossroads' referral network for dental practice clients.
• Pain Free Dental MarketingminorStrategic or Co-development PartnerEric Hubbard discusses marketing firm approaches, defining success metrics, timing for hiring a marketing firm, and how to get started. Collaborates with Crossroads' dental practice client advisory team.
• Joe Hess LawminorStrategic or Co-development PartnerJoe Hess provides healthcare legal counsel for dental practices, including upfront organization and reasons to have legal representation as part of the practice advisory team.
• Larry Guzzardo (Practice Management Consultant)minorStrategic or Co-development PartnerPractice management consulting for dental practices, helping clients understand when and why to engage a consultant and how to select the right fit. Part of Crossroads' dental practice advisory ecosystem.
• Dental Dollars & SenseminorStrategic or Co-development PartnerDoug Fettig provides strategic coaching for dental practices. Jason Hite from Crossroads discusses importance of having a strategic coach for dental practice success. Part of comprehensive advisory approach.

Scale indicators2 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Anders CPAs + Advisors: Mid-sized regional CPA and advisory firm with a dedicated healthcare industry group serving dental practices, medical groups, and healthcare entrepreneurs. Most directly comparable to Crossroads in combining vertical healthcare specialization with closely held business advisory and tax planning.

Broad incumbents

• BDO USA: Top-5 global accounting network with a U.S. healthcare practice serving dental and medical groups, including private equity-backed dental service organizations. Comparable in healthcare vertical specialization, but operates at scale with full audit, tax, and consulting capabilities.
• Wipfli LLP: Top-20 U.S. accounting and advisory firm with a sizable healthcare practice serving medical groups, dental practices, and dental support organizations. Comparable to Crossroads in healthcare vertical specialization but operates at vastly greater scale with audit, consulting, and technology capabilities.
• CliftonLarsonAllen (CLA): Top-10 U.S. accounting and advisory firm with a dedicated healthcare industry group providing tax, accounting, and advisory to dental and medical practices. Comparable in healthcare-vertical focus, but operates at much greater scale across multiple regions.
• Withum: Top-30 U.S. accounting and advisory firm with a healthcare practice serving dental practices and medical groups. Comparable through its healthcare-focused services and closely held business expertise, though substantially larger and more diversified than Crossroads.
• RSM US LLP: Top-5 U.S. accounting firm with a healthcare industry practice serving dental groups, private equity-backed dental platforms, and other healthcare providers. Comparable through healthcare specialization and tax advisory but with substantially broader capabilities including audit and transaction advisory.
• Eide Bailly LLP: Top-25 U.S. accounting firm with a recognized healthcare industry group providing tax, audit, and advisory services to dental and medical practices. Comparable through its healthcare-practice focus but at materially larger scale and broader service menu.
• Plante Moran: Large U.S. accounting, tax, and consulting firm with a healthcare practice serving dental and medical groups across multiple states. Comparable in healthcare-vertical services but offers significantly broader resources including audit and consulting practices.
• Forvis (formerly BKD + Dixon Hughes Goodman): Top-10 U.S. accounting firm formed from the BKD and DHG merger, with a large healthcare industry group serving dental practices, hospital systems, and medical groups. Comparable vertical specialization but at much larger scale and broader geographic footprint.
• Marcum LLP: Top-15 U.S. accounting and advisory firm with a healthcare practice serving dental practices, ambulatory care, and healthcare entrepreneurs. Comparable in combining vertical specialization with closely held business advisory, though at much larger scale.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks7 records

Key highlights7 records

Customer concentration

• Xx.com/taxcrossroads

Revenue estimate

Valuation estimate

Number of profiles

Profiles14 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Crossroads Tax Advisors