Oregon CPAs, insurance billers and affordable help on Upwork

This lesson is three lists and the checks that go with them. First, ten Oregon CPA firms, grouped by region, each run through the Oregon Board of Accountancy's license lookup. Second, nine insurance billing services, six of them based in Oregon, the six Oregon firms checked against the state business registry, and all nine against the federal exclusion list. Third, Upwork, which is where I would send a solo therapist who needs bookkeeping or billing help at a price a new practice can carry, with the fees and the one HIPAA trap spelled out. I checked every page and license in September 2026; the Board's data was stamped September 30. Nothing here is an endorsement. A firm's claims are reported as the firm's claims, and the vetting sections exist so you can run the same checks yourself. The video above is Upwork's own walkthrough of posting a job and hiring; it does that part well and skips fees and HIPAA, which the Upwork section below covers.

Before you hire a CPA

Start with the Oregon Board of Accountancy licensee search, reached from the Board's Licensee Look-up page. A result shows the license number, status, type, date granted, expiration, firm, and a Disciplinary column that reads yes or no. The Board's advice on that page: "make sure the license is current, and inquire whether there have been any disciplinary actions against the licensee", and "Only persons who are licensed may call themselves a Certified Public Accountant or Public Accountant." Individual licenses expire June 30; firm registrations expire December 31 of odd years. When the Disciplinary column says yes, cases since 2011 are in the Board's Disciplinary Action Report, a spreadsheet covering January 1, 2011 to February 4, 2026; for anything older, call the Board; the page gives (503) 378-4181.

Two things the lookup will not settle. A CPA who practices alone need not register a firm: ORS 673.160 requires registration for a business that uses the CPA title, and subsection (2) exempts a single Oregon licensee practicing alone unless the person holds out as a multi-licensee organization or does attest or compilation work. A missing firm registration is therefore a question ("is it just you?"), not a finding. And a CPA licensed in another state may lawfully serve you under ORS 673.153, the mobility section, with no Oregon notice or fee; verify that person with their home-state board instead.

Then the engagement letter. The Board again: "Talk frankly with a CPA/PA about fees. It is important to make certain before any work is done that you receive an engagement letter detailing the work to be performed for you, who will specifically be performing the work, and the cost of the service". It also suggests asking whether the firm has non-CPA owners and whether the licensee can be reached later in the year if you need help with an audit. The AICPA's How to Choose a CPA adds "What type of clients make up most of your practice?", "Can I call you for advice during the year?" and "Are there clients I can contact for references?", and says "The best time to interview CPAs is in the summer and fall". For a therapist the first of those is the one that matters. You want someone who already files for one-owner service businesses, and ideally for therapists.

Three credentials other than CPA come up in Oregon, and they are not interchangeable. Anyone who prepares Oregon personal income tax returns for pay must, in the words of the Oregon Board of Tax Practitioners, "be Licensed or Registered with the Board of Tax Practitioners". The Board issues two licenses. A Licensed Tax Consultant (LTC) can prepare and sign your return on their own. A Licensed Tax Preparer (LTP) may work "only under the supervision of a tax consultant" or a CPA or attorney, per ORS 673.615(2). The statute defines both around personal income tax returns, so if you file an S corporation return, ask whether the person prepares entity returns at all. Check either license in the Board's license lookup. The third is the enrolled agent, a federal credential the IRS calls "the highest credential the IRS awards", earned through a three-part IRS exam or IRS employment, with 72 hours of continuing education every three years and the same unlimited practice rights as a CPA. Since June 5, 2026, the Board's homepage says, SB 1510 lets an enrolled agent register as a Registered Enrolled Agent and work on Oregon personal returns for a fee without the state exam or continuing education. The NAEA keeps a Find a Tax Expert directory.

The IRS sets the floor low: "Anyone can be a paid tax return preparer as long as they have an IRS Preparer Tax Identification Number (PTIN)", per its Choosing a tax professional page. Its Directory of Federal Tax Return Preparers is searchable by name and location for attorneys, CPAs, enrolled agents and other credential holders with a valid PTIN. Its February 2026 tax tip is blunt: "avoid tax return preparers who base their fees on a percentage of the refund", "Never sign a blank or incomplete return", and "Paid preparers must sign and include their PTIN on any tax return they prepare." The Oregon Society of CPAs runs a Find-a-CPA search with Medical Professionals and Health Care filters; it says of itself that "this is a referral, not a recommendation" and that it cannot promise a listed firm is taking clients.

On fees there is no Oregon survey. The nearest thing is the National Society of Accountants' 2020–2021 Income and Fees Study for the Pacific region, now about five years old and drawn from a sample that leans toward enrolled agents and unlicensed preparers rather than CPAs. Its averages: $432 for an itemized Form 1040 with a state return, $275 for a Schedule C on top, and $1,223 for an 1120-S. The NSA's 2024 national summary (183 respondents) puts an itemized 1040 at $300 to $600 and a Form 1120 at $750 to $1,250, with no figure for an S corporation. Read these as a dated floor. The two firms below that publish prices are the only current Oregon numbers I have.

Ten Oregon CPA firms, by region

These are compiled by my own research. I personally did my own taxes and Billing for CUTI using a harness I built specifically for accounting. I have had great experiences with Jones and Roth for my real estate portfolio. Salem, Eugene, Bend, Portland and Medford. Seven of the ten show healthcare or therapist work on their own sites. The other three (Thunderegg in Portland, Fowler in Bend, Hokinson in Medford) are general small-business firms listed so that each region has an option; nothing on their sites mentions healthcare. License facts are from the Board lookup on September 30, 2026, and prices are the firms' own published figures on the same day. Where I write "ask," the public record left a question open.

Jones & Roth PC, Eugene, Bend and Hillsboro

A mid-size firm with a healthcare group that describes "Partnering with Physicians and Managers" and a "Healthcare Practice Success Plan"; its lead is Nicole McOmber, CPA. Offices, per the contact page: Eugene, Bend and Hillsboro. Board: firm #263, active, expires December 31, 2027, Disciplinary yes; Nicole Catherine McOmber, #11441, active, expires June 30, 2027, no discipline. The firm's record is Case 21-008, a settlement dated February 17, 2022, for "employing and allowing a lapsed licensee to practice public accountancy prior to becoming actively licensed in Oregon", with a $1,500 civil penalty and $1,000 in costs; the order suspended $750 of the penalty and all of the costs pending compliance, leaving $750 to pay; the Board's report has the full entry, and you should read it yourself. Disclosure: I use Jones & Roth for my real estate portfolio, not for the practice. No published prices. For Bend readers it is the only firm on this list with both a Bend office and healthcare copy.

Gates Tax & Advisory, Portland

The homepage lists "Mental Health Professionals" under Health and Medical, next to massage therapists, chiropractors, doctors and dentists, and the FAQ says the firm supports LLCs, S corps and multi-state issues. Published prices are medians rather than minimums: "Individual Returns: estimated median price $1,500 billed annually", business returns at a $2,200 median, tax planning at $600 to $1,500 a year, and advisory at $280 an hour, the high end of this list for a solo practice. Board: the site prints no license number; the lookup shows Joseph Dale Gates, CPA #14862, active, expires June 30, 2028, no discipline, in Canby, which matches the founder's name and town but is a name-and-city match rather than a confirmed number, so ask for it. No firm registration was found, while the site speaks of its CPAs in the plural; ask whether the firm is registered under ORS 673.160. The firm was founded in July 2024.

Metzger Advisors (formerly Metzger Tax Service), Portland and Tigard

A family-owned CPA firm since 1962, by its own account, whose healthcare page promises "specialized accounting and tax services for Portland's medical community"; the examples are physicians and dentists, not therapists. Staff include CPAs, an LTP and an enrolled agent. No published prices; the FAQ says a written proposal follows the first consultation. Board: firm #3123, registered as Silkwood Tax Services LLC doing business as Metzger Tax Service, active, expires December 31, 2027, with three active CPAs. One of them, Robert Sederstrom Jr, #4437, shows yes in the Disciplinary column; the case is not in the Board's 2011 to 2026 report, so it likely predates 2011, and the Board can tell you what it was. Read the record before deciding what it means.

Thunderegg Accounting LLC, Portland (general small business)

The homepage describes "income tax services for small businesses, small non-profits, and individuals" with a focus on creative professionals, and prints its own registration: "an Oregon-registered CPA firm, firm license #2922." Board: firm #2922, active, expires December 31, 2027, no discipline, with CPAs Jeffrey Kyle (#16095) and Katherine Ressler (#15549). No prices. The homepage still showed an April 2025 notice that the firm was not taking new clients for that filing deadline, so ask whether it is taking them now.

Aldrich CPAs + Advisors LLP, Lake Oswego

A large regional firm whose healthcare page is headed "Healthcare Accounting & Financial Services for Doctors & Physicians" and speaks to "private medical practices." Board: firm #2086, active, expires December 31, 2027, no discipline. No prices. More firm than a one-clinician practice is likely to need; listed because its healthcare work is explicit.

Gerald Hoots CPA PC, Salem

The homepage addresses "a medical practice, dental office, or healthcare facility" and offers bookkeeping, payroll and tax planning; it does not mention therapists. Board: Gerald E. Hoots, CPA #3327, active, expires June 30, 2027, no discipline, licensed since 1979. The firm search returns no registration, though his individual record names Gerald Hoots, CPA, P.C., which is fine for a sole practitioner; ask. A license that old also makes succession and backup coverage a fair question. No prices.

Isler CPA LLC, Eugene

Its professional services page groups medical practices with law firms, engineering firms and real estate agencies as service businesses that need "forward-thinking tax and accounting strategies." Board: firm #1962, active, expires December 31, 2027, no discipline. A related registration, Isler Medford LLC (#1964), is also active; its site would not render for me, so I cannot say what it offers. Do not confuse either with The Isler Group in Klamath Falls (#1963), a different firm. No prices, and no therapist-specific copy.

Fowler & Co., Inc., Bend (general small business)

The small business page lists "Weekly, monthly or quarterly bookkeeping including posting, reconciling and reviewing your books" among its services; there is no healthcare page. Board: firm #2491, active, expires December 31, 2027, no discipline; Gregory S. Fowler, #9522, active, expires June 30, 2028. No prices.

Hokinson CPA PC, Medford (general small business)

The homepage calls it "a full-service Accounting firm licensed in OR" serving "business owners, executives, and independent professionals." Board: firm #2365, active, expires December 31, 2027, no discipline; Todd R. Hokinson, #9608, active, expires June 30, 2028. No healthcare page and no prices. This is the thinnest fit on the list. No Medford or Ashland firm with readable healthcare copy turned up, so a southern Oregon therapist may do as well with a Eugene or Portland firm that works remotely.

Breath and Taxes LLC (Nicole Long, CPA), Portland

The one firm here whose own FAQ lists "Private practice therapists" first among the industries it serves, ahead of wellness businesses and contract workers; a client testimonial on the site mentions an S corp transition for a therapy practice. Published prices: Form 1040 from $175 single or $300 joint, an additional state return $50, Form 1120-S from $650, a monthly review at $150 for a sole proprietor or $225 for an S corporation, S-corp formation $800, and consulting at $200 an hour; clients who qualify for the earned income credit get a 10 to 50% discount. Board: Nicole Pui-Ling Long, CPA #15162, active, expires June 30, 2028, no discipline, which matches the license number the site prints. No firm registration, consistent with one licensee practicing alone. Capacity is the catch: "Every Q3 Nicole assesses how much capacity she has and how many additional tax returns/clients she can take on", so ask early. The homepage also carries a political statement.

Before a biller touches a claim

A billing service is a HIPAA business associate. HHS's business associate guidance lists "claims processing or administration, data analysis, billing, and practice management" among business associate functions, and the contract comes before the data: a covered entity may disclose PHI to a business associate only after it "obtains satisfactory assurances, in the form of a contract or other written arrangement", the business associate agreement, or BAA. The biller's own subcontractors need a BAA with the biller before they see anything, which makes "who else touches my claims, and do they sign too?" a fair question. HHS publishes sample BAA provisions with the ten required elements. One of the nine firms below says on its site that it signs a BAA with each practice and one more has BAA terms in its contract; the rest say nothing either way, which is not a refusal. Ask for the BAA before the first client name leaves your EHR. The HIPAA lesson covers what the agreement has to contain.

Run the exclusion checks. HHS's Office of Inspector General keeps the List of Excluded Individuals and Entities, and its exclusions page explains the stakes: "Those that are excluded can receive no payment from Federal health care programs for any items or services they furnish, order, or prescribe", and "Anyone who hires an individual or entity on the LEIE may be subject to civil monetary penalties". Search the firm and each person who will handle your claims at exclusions.oig.hhs.gov. Oregon keeps a shorter list of providers barred from serving Oregon Medicaid clients on OHA's Provider Enrollment page, under Sanctioned Providers; it held three entries at the end of September 2026, so it supplements the federal list rather than replacing it. None of the nine firms below appeared on either list on September 30, 2026. I searched the named owners too; the only hits were same-name individuals in other states, which a name-only search cannot resolve, and TheraThink names no owner to search. A name-only match on a common surname settles nothing; the OIG search can confirm an individual only with identifiers the hiring party supplies.

If you bill the Oregon Health Plan, there is a state enrollment question. Under OAR 410-120-1260, a billing service that only submits claims is a non-payable provider type, "a billing agent or billing service submitting claims or providing other business services on behalf of a provider but not receiving payment in the name of or on behalf of the provider." A service that will receive or direct your payment must be "enrolled with the Oregon Health Authority to provide services with the submission of claims and to receive or direct payment in the name of the rendering provider pursuant to 42 CFR 447.10(f)", and electronic submitters register as EDI trading partners under OAR 943-120. Ask whether the firm is enrolled with OHA as a billing agent, and whether OHP money will ever pass through its accounts. The payer contact sheet has the OHA enrollment page itself.

Then the offshore rule, stated exactly, because vendors state it loosely. Federal Medicaid law, 42 U.S.C. 1396a(a)(80), requires that the state "shall not provide any payments for items or services provided under the State plan or under a waiver to any financial institution or entity located outside of the United States." CMS's 2010 letter to state Medicaid directors draws the line: payments for "outsourcing information processing related to plan administration or outsourcing call centers related to enrollment or claims adjudication are not prohibited", while payments "to financial institutions or entities such as provider bank accounts or business agents located outside of the U.S." are. So the law bars OHP money from flowing to an offshore entity; it does not, by its own text, ban an offshore team from keying your claims. I did not review individual CCO provider agreements or commercial payer contracts, which can add their own terms. The practical rule for OHP work: hire a biller whose people and payment entity are in the United States, and get "all work is done in the US" in writing. Two of the Oregon firms below say as much on their sites.

Give the biller their own login, with the narrowest role, and never share yours. In SimplePractice, the practice biller role is free, but "Adding team members is only available on the Plus plan" ($99 a month, against $49 Starter and $79 Essential); billers "have limited access to all client profiles" and "can manage billing documents, payments, billing reports, and payroll for all clients", and see chart notes only if you grant that separately. In TherapyNotes, a Practice Biller "has full access to billing" but is "not able to see clinical notes"; non-clinical users are unlimited on the $79-a-month first-clinician plan; and the help center is explicit that "No two people should be using the same login credentials", which is a terms violation and ruins the audit trail. Some services file from their own system instead (TheraThink says claims go out "through your TheraThink account"), and then the question is how your client data gets there, which is the BAA question again. The SimplePractice setup lesson covers the account itself.

Credentials are easy to check and worth asking about, though no rule requires them. Oregon has no license for medical billers that I could find, and none of the nine firms below claims a named credential for its staff. The common ones are AAPC's Certified Professional Biller (CPB) and Certified Professional Coder (CPC), which AAPC will verify "with a member's ID# and last name".

On price: among the firms below that publish one, the range is 4 to 7% of collections, with monthly minimums and add-on fees that raise the effective rate for a small caseload. That describes these specific firms. I found no credible survey of billing fees; the "industry average" figures on vendor blogs trace to no primary source. Compare quotes on the same lines: percentage of what (net collections, allowed amount, or gross charges), any monthly minimum, separate fees for credentialing, eligibility checks, statements and old receivables, the contract term, and how you leave. The superbills lesson is the do-it-yourself route for a mostly self-pay caseload.

Nine billing services

Six are based in Oregon and three are not. The three out-of-state firms are labeled by home state, because an "Oregon" landing page is not an Oregon office. Facts are from each firm's own site, and for the Oregon firms the state business registry, on September 30, 2026. "No published pricing" means the number is not on the site, nothing more.

Psychotherapist Billing Services, Eugene

A street address in Eugene (1200 High Street, Suite 130) and the longest history on the list: "Established in 1987, Psychotherapist Billing Services is a professional billing company based in Eugene, OR. We specialize in mental health billing", serving "practices throughout Oregon and the west coast", per its site. Its managing member is described as having managed-care experience "from the payer side, particularly with Oregon Health Plan." It states that "a Business Associate Agreement is created with each practice" and that staff complete periodic criminal background checks and annual HIPAA and CMS training. No published pricing ("competitive pricing"); benefit checks and credentialing are billed separately. Registered as an Oregon LLC since 2011.

Advanced Billing Solutions, Oregon

Disclosure first: this firm has a partner page on this directory. It was vetted exactly like the others. Its site describes "expert medical billing services for mental health providers throughout the State of Oregon", and on staff location it is the clearest firm on this list: "No Overseas Outsourcing: We handle all billing services in-house", with a HIPAA compliance statement beside it. No published pricing ("No Hidden Fees" is the only wording) and no BAA statement on the site, so ask for one. The state registry lists the LLC as registered in October 2025 with a Portland address, while the site gives Klamath Falls, so ask which office does the work. Mental health only.

AdvanceAPractice, Portland

"Portland based support for Oregon behavioral health and outpatient practices", per its site, which has a page on Oregon behavioral health payers and says "Our own team here in the United States does your work." Pricing is published and is the highest on this list: "Core RCM is 7% of collections with a $500 monthly minimum per provider", credentialing at $500 per commercial payer per provider, and a $497 credentialing gap report. The minimum is the number to notice: below about $7,100 a month in collections ($500 divided by 0.07), the floor costs more than 7%. No BAA statement; the privacy policy says client privacy is "addressed in the applicable service agreement", so ask to see that agreement. No street address on the site. Registered as an Oregon LLC in 2023.

Swift Medical Solutions, Bend

A street address in Bend, and mental health is one service line among several: its mental health billing page says it supports "psychologists, psychiatrists, and therapists". Pricing is published: "Swift charges 4-7% of monthly net collections, depending on specialty and claim volume. There are no setup fees, no per-claim charges, and no software costs." It describes having built "compliance and HIPAA programs from the ground up"; no BAA statement, and no statement on where staff sit. The Oregon registry's active entity is Swift MDS LLC, registered in 2024, while the site's footer says Swift Medical Solutions, LLC; ask for the legal name that will be on your contract.

PDXPERT Medical Billing, Portland (Jane App users only)

Read the limit first: "Unfortunately, we only offer claims and billing services for Jane App users." Its site leads with chiropractors, naturopaths, acupuncturists and massage therapists, then adds that it also handles claims for "mental health therapists." Pricing is a custom flat monthly quote, "valid for six months, reassessed biannually", with no number published. It states HIPAA measures, adherence to OIG rules for billers, errors and omissions insurance, and American Medical Billing Association membership; no BAA statement. Registered as an Oregon LLC in 2021.

MindEase Billing, Springfield and Clackamas (PO box only)

Its site says it bills "for mental health practitioners in solo practice, primarily in Oregon", then narrows: "Though our expertise is in serving MDs and MHNPs, we sometimes have openings for psychologists and counselors as well", and it is not taking groups. The only address is a PO box in Springfield; the footer reads Clackamas and has not been updated since 2024. No published pricing, and no BAA or HIPAA statement found. Registered as an Oregon LLC since 2009. For a counselor, openings are occasional by the firm's own words.

Bomi Health (Illinois)

Based in Champaign, Illinois, per its terms, with an Oregon page that mentions "OHP and CCO setup" and says plainly that "Bomi supports therapy practices in every state across the U.S. This page highlights Oregon-specific setup and payer context." Its pricing is the clearest on the list: "4% of net collections. Month-to-month.", "$50 per insurance company / therapist. First four free", invoiced at month end on collections actually received, and no billing fee if you leave during onboarding or the first month. It says it works inside SimplePractice, TherapyNotes, Sessions Health and TheraNest. Its terms include BAA language and address 42 CFR Part 2. Where its billing staff sit is not stated; "Bomi is located in the United States" describes the company. Ask before signing if OHP claims are involved.

TheraThink (Washington)

Seattle-based, per its FAQ, serving "therapists all across the United States", and "Billing Exclusively for Mental Health Professionals". It charges a percentage of the allowed amount on paid claims only, and does not publish the percentage; every provider pays "$35 / month / unique tax ID + rendering NPI" in months with claims; no startup or per-claim fees. Credentialing prices disagree between pages ($130 or $140 per commercial panel, $270 for Medicare), so get a written quote. Claims are filed "through your TheraThink account", not from inside your EHR. HIPAA wording only, no BAA statement, and no mention of Oregon or OHP anywhere on the site.

Resolute Billing (Arizona)

An Arizona firm with an Oregon landing page, one of about 29 state pages, that names Oregon payers and lists Portland, Eugene, Salem, Bend and Medford. Its focus is "mental health and substance-use programs", and the services described are for IOP, PHP, residential and detox programs, a weak fit for a solo practice. No street address on the site, no pricing, and no BAA or HIPAA statement.

Upwork, where the affordable help is

Upwork is a marketplace of freelancers, paid through Upwork's escrow, with client reviews and earnings history attached to every profile. For a solo practice it works for two jobs: monthly bookkeeping (categorizing a bank feed, reconciling, producing a profit and loss report your CPA can read) and claims work (submitting, chasing denials, posting payments). Both repeat every month and can be scoped to a fixed deliverable, and there is a deep pool of people who do nothing else. What follows is the fee structure, what the badges mean, the settings that matter for a healthcare client, and the HIPAA trap built into the time tracker.

What it costs

Upwork's client pricing page says the free Basic plan carries a "5% service fee. For example, a $100 contract would cost $105 in total + contract initiation fee." That initiation fee is "ranging from $0.99 to $14.99", charged once per new contract (a rehire counts as new; adding a milestone to an existing contract does not), so one ongoing contract with milestones beats a string of small ones. Upwork's own pages disagree on the percentage: its help center says the fee is "up to 7.99% on all payments you make to freelancers", and the fee agreement on its legal page says the rate "can vary". Read the fee line on the offer screen before you click. US clients who pay by bank account get 3% instead of 5%, but only after $1,000 spent on Upwork in the past 12 months, with on-time payments and a backup billing method on file. Worked example: a $300 fixed-price month of bookkeeping at 5% is $315, plus the initiation fee the first month. At 7.99% it would be $324.

One more fee lives in the terms. Upwork's Conversion Fee article says the terms "require you to keep all work and payments on Upwork for the first two years". Taking a freelancer off the platform sooner means paying "13.5% of a freelancer's hourly rate x 2,080 hours", which Upwork's own example puts at $8,424 for a $30-an-hour freelancer, and doing it without paying risks account suspension. Keep payment on Upwork. It also keeps the tax paperwork simple, as below.

What the badges mean

In Upwork's words. The Job Success Score "reflects client satisfaction, contract outcomes, and long-term client relationships", is updated daily over 6-, 12- and 24-month windows, and the article calls 90% or above high and below 79% low, without naming the band between. It is not a star average, and a new freelancer has none, so 100% across three small contracts says less than 95% across forty. Among the talent badges, Rising Talent requires, with other conditions, a 4.8 average rating and at least $250 earned in the past year. Top Rated is "top 10% of talent": a 90% or better score for 13 of the last 16 weeks and $1,000 earned in a year. Top Rated Plus is "top 3%", with $10,000 earned and a large contract. Expert-Vetted is "top 1%", typically invitation-only, after a 30-minute interview, in select categories. Badges are lost for moving work or payment off the platform.

What Upwork verifies, and what it does not

Upwork verifies identity and location. The pricing page: "Upwork verifies every freelancer's identity and location before you connect", and the blue check next to a name means Upwork has "taken steps to verify your identity." It does not verify a CPA license or a billing credential. A freelancer types a license into their profile with a "Licensing verification URL ... where your license can be verified by clients". So the check is yours: a CPA through that state's board lookup (Oregon's is above), a CPB or CPC through AAPC's credential verification. And remember the Oregon rule from the CPA section. A non-CPA who prepares your Oregon personal return for a fee must be licensed or registered with the Board of Tax Practitioners, so an Upwork tax preparer in another state may not be allowed to prepare it at all.

US only, and why that matters for OHP

In talent search, "select the 'U.S. only' filter in the sidebar first, then filter further by state, city, and time zones." On a job post, choosing U.S. only means "only freelancers in the U.S. will be able to see your post and submit a proposal"; a state preference such as Oregon stays a preference, because "freelancers anywhere in the U.S. can still see and submit." Use the filter for anyone who will touch OHP claims. The offshore rule above is the reason: Medicaid payments to an entity outside the United States are barred, and while the statute does not itself ban offshore data entry, a freelancer abroad handling your Oregon Medicaid claims leaves you explaining that distinction to a CCO. Keep it domestic.

What people charge

Upwork publishes "typical hourly rate ranges of certain historical contracts worldwide", with no sample size, date window or method, and adds that what clients pay "is subject to negotiations with talent." Its figures, as of September 2026:

Role	Upwork's published range
Bookkeepers	$11 to $25 an hour
Accountants	$12 to $32 an hour
Certified public accountants	$19 to $70 an hour
Tax preparers	$40 to $80 an hour
Medical billers	No published range

The medical billers page shows a handful of profiles, some outside the US, which is a sample and not a range. Because the ranges blend offshore and US talent, a US-only search will land at or above the top of each. Many billers price as a percentage of collections rather than by the hour, and Upwork has no data on that.

Hourly or fixed price, and what Hourly Protection covers

A fixed-price contract funds a milestone into escrow (minimum $5) and "Work is submitted for your approval before funds are released"; you have 14 days to approve, ask for changes, or dispute; do nothing and the funds release. An hourly contract can carry a weekly hour cap and a choice of tracked or manual time, billed weekly. Hourly Protection sounds like a guarantee and is not. The hourly payment agreement on the legal page requires that "Both Client and Freelancer must agree to use Work Diaries", and it "only protects Client from the obligation to pay for Freelancer's work if the documented hours worked are not clearly related" to the job. The same agreement says "Disputes handled by Upwork can only address the hours billed, not the quality of the Freelancer Services." Sloppy books or wrong claims are covered by nothing. Quality protection on Upwork is a fixed-price milestone you review before you release it.

The time-tracker trap

Tracked time means Upwork's desktop app "takes random screenshots and monitors keyboard keystrokes and mouse activity." Its software license says those screenshots "may include ... the visual output of all open programs, windows ... and any information, images, and text therein", and that confidential information on screen "may be included in a Screenshot, transmitted to Upwork, and displayed in the applicable work diary." A biller working inside your EHR on a tracked hourly contract is sending screenshots of client records to a company that has no BAA with you. For anyone who will see PHI, use fixed-price milestones or manual time (which has "No screenshots or activity logs"), and accept that "Manual time is not covered by Hourly Protection." A bookkeeper who sees only deposits, totals and expenses may need no PHI at all; design the work that way, and ask your own advisor whether payer remittance detail counts as PHI in your setup.

No BAA from Upwork

Upwork's legal page contains no business associate agreement for marketplace clients, its help center returns nothing for "HIPAA", and its integration terms bar transmitting "protected health information under HIPAA" through its integrations. Any NDA or side agreement is between you and the freelancer; Upwork "does not review, enforce, or become a party to these agreements." So before any PHI moves, sign your own BAA directly with the freelancer, using the HHS sample provisions above as the floor. Keep PHI out of Upwork messages, files and job posts; share it only inside your EHR, through the freelancer's own login and the narrowest role. Upwork's job rules bar "Jobs for medical treatment or diagnosis"; billing and bookkeeping are allowed.

No 1099-NEC for Upwork payments

You do not file a 1099 for someone you pay through Upwork. Upwork's help center: "you don't have to file tax forms like the W-2, 1099-MISC, or 1099-NEC", because you are paying its licensed escrow subsidiary, a third-party settlement organization that reports on Form 1099-K. The IRS instructions for Forms 1099-MISC and 1099-NEC say the same: "Payments made with a credit card or payment card and certain other types of payments, including third-party network transactions, must be reported on Form 1099-K by the payment settlement entity under section 6050W and are not subject to reporting on Form 1099-MISC or Form 1099-NEC." The fees and payments are ordinary business expenses; how to book them is your CPA's call. If you ever pay the same person directly, off the platform, the normal 1099-NEC rules apply to those payments (the hiring and payroll lesson covers contractor paperwork), and the Conversion Fee applies too.

A sample job post

Upwork's post form asks for a title, three to five skills, scope, experience level, location, a budget, and a description, and it is against the terms to share contact information before a contract. Name the software, the payers, the volume, and the credential; leave out client details. A Basic job post comes with 30 free invites, so search US only, filter by badge and rate, read reviews from clients who sound like you, and invite a shortlist rather than waiting for proposals. For billing, something like this:

Insurance billing for a solo Oregon therapy practice (US only). Monthly claims for one clinician in SimplePractice, roughly 60 sessions a month across three commercial payers and one OHP CCO. Scope: submit claims weekly, work denials, post ERAs, send a monthly aging report. Fixed price per month, paid as a milestone after I review the report. CPB or CPC preferred. You get your own SimplePractice biller login; no client data in Upwork messages. A signed BAA is required before access.

Pay for a small test

Upwork prohibits "Asking freelancers to work for free" to win a job, so the test is a small fixed-price contract. Give them one month of a made-up bank register to reconcile, or a short list of denied claims you invent for the purpose, with fake names and fake policy numbers. Never use real client data in a test; there is no BAA yet, and nothing in the result is worth a breach. Read the work the way a CPA or a payer would, then offer the real contract. The bookkeeping basics lesson describes the monthly close you are hiring for.

My split

Upwork for the bookkeeping and the billing help: monthly, repeatable, scoped as fixed-price milestones, US only, with a BAA and the freelancer's own EHR login before any client name is shared. A licensed Oregon CPA, or an Oregon-licensed tax consultant or an enrolled agent, for the return itself, because that is where Oregon's licensing rules apply and where someone has to sign with a PTIN. Never send a Social Security number or any client information before the contract and the BAA are signed. Keep every payment on Upwork. And whichever route you take, the entity lesson is the conversation to have with the CPA first, since the answer changes which return you are paying for.

None of this is legal, tax or accounting advice. I recorded what each page and lookup said on the day I read it. A license can lapse and a price can change the following week; the Board lookup and the firm's own written quote outrank this list.

Further reading

• Oregon Board of Accountancy: Licensee Search. The lookup every CPA entry above was run through; ten seconds per name.
• Oregon Board of Tax Practitioners. Who may prepare an Oregon personal return for pay, the LTC and LTP licenses, and the 2026 Registered Enrolled Agent change.
• HHS: Business Associates. Why a biller is a business associate and why the BAA comes before the data.
• HHS OIG: Exclusions. The penalty for hiring an excluded person, and the link to the online search.
• Upwork: Pricing for clients. The fee page, to be read alongside the fee shown at checkout.
• IRS: Quick tips for picking a tax pro. The percentage-of-refund warning and the PTIN signature rule.