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QuickBooks

Why This SWAT Team CFO Says Your Legacy Systems Are Costing You Millions

Earmark Team · January 28, 2026 ·

When Ximena Velazquez Maynard stepped into her role as CFO of Legacy Management Group in early 2023, she found exactly what she expected: a disaster. The company was juggling 30 separate QuickBooks files while their 11 nursing homes operated in a financial system where facilities couldn’t even talk to each other. Basic financial tasks that should take hours were consuming months.

But for Velazquez Maynard, this was familiar territory. Throughout her career, she’s been the “SWAT team” CFO who gets called in when companies need their accounting rescued, she explains in episode 32 of The Unofficial Sage Intacct Podcast. And she’s turned several of those disasters into companies that sold for huge profits within just a few years.

A Healthcare Empire Built on Shaky Financial Foundations

Legacy Management Group’s story begins in the 1980s with two nursing homes run like a mom-and-pop operation. Everything changed in 2018 when the current leadership took over with a vision to do something greater.

Since then, Legacy has expanded to 11 nursing facilities (nine in Louisiana, two in Texas), plus a pharmacy and mobile X-ray company. They have five holding companies, property companies, and a management company, all with slightly different ownership structures that need to stay separate for legal and financial reasons.

When Velazquez Maynard arrived, she inherited a patchwork of systems trying to manage this complexity. The 11 nursing homes were using PointClickCare’s financial module—a system so limited that facilities in the same software couldn’t communicate with each other. “It was not created by a very good accountant,” Velazquez Maynard says bluntly.

The remaining entities were scattered across QuickBooks files. At one point, they had 30 separate files to manage.

When Manual Processes Strangle Growth

The impact of these disconnected systems went far beyond inconvenience. Consider what happened when Legacy needed to split a bill among their 11 facilities. The accounting team had to make 11 different entries into 11 different files, plus create corresponding due-to and due-from entries. “They would never, ever reconcile in the end,” Velazquez Maynard recalls.

The lack of visibility created expensive blind spots. Floor spending requirements—a critical metric where nursing homes must spend a specific dollar amount per resident annually—went untracked. Without proper monitoring, Legacy once found themselves owing $300,000 to the government because they couldn’t see their spending trends across facilities.

“We could not see easily on a month-to-month basis where we were trending on our floor spending requirement per facility, which varies greatly,” Velazquez Maynard explains. This meant they couldn’t make informed decisions about staffing levels or resource allocation until it was too late.

During her interview for the CFO position, Velazquez Maynard didn’t sugarcoat the situation. “I hear your issues, I hear what you’re doing. It’s not working because you don’t have the software you need.” Within three months of starting, she confirmed the current setup couldn’t support Legacy’s growth plans.

The Complexity of Healthcare Finance

Healthcare organizations face unique challenges that make financial management particularly complex. Legacy deals with monthly audits, manages resident trust funds under strict regulations, and navigates billing across Medicare, Medicaid, hospice companies, and workers’ compensation.

“It’s a very complicated system,” Velazquez Maynard notes. The company often guides families through Medicaid applications that can take one to six months while providing care regardless of payment status. They serve some of society’s most vulnerable populations, including residents without family who cannot make their own decisions.

The St. Christina facility acquisition shows how operational and financial challenges intertwine. When Legacy bought this facility with “the absolute worst reputation,” Velazquez Maynard discovered a wheelchair ramp that, instead of being repaired, had padding on the adjacent wall to catch wheelchairs that might slide into it. “I was amazed. I was like, this is terrifying,” she recalls.

Legacy invested millions transforming the facility, adding private bathrooms and making it safer for residents. But such strategic investments require a level of financial visibility that’s impossible with 30 separate QuickBooks files.

A Rapid Transformation

Having implemented Sage Intacct eight years earlier at NTT Testing, Velazquez Maynard knew what was possible. This time, the implementation was even faster. “We implemented everything within two to three months,” she confirms.

The team kept it simple, using core Intacct functionality rather than trying to do too much at once. “We wanted to get everything in there. We got all the basics in flowing well first, and then we looked at adding purchasing and other things that may be available to us,” Velazquez Maynard explains.

The transformation wasn’t without challenges. Legacy invested in EMRConnect to pull financial and statistical data from PointClickCare into Intacct, hoping for complete visibility through dashboards and reports. Unfortunately, that integration hasn’t delivered as promised. “The most we’re getting out is basically journal entries coming over,” Velazquez Maynard admits. “That’s probably been our only challenging point throughout the integration.”

Despite this setback, the core implementation delivered immediate wins. Within months, Velazquez Maynard created custom floor spending reports that transformed how Legacy manages compliance. “It’s an easy report that we can look at every single month. And we do. We analyze it,” she says. “Each quarter, we’re able to make informed decisions on staffing.”

Life-Changing Automation

The most dramatic improvement came from Sage Intacct’s handling of inter-entity transactions. What once required hours of manual entries and reconciliation now happens automatically in the background.

“One thing that was life changing for us was the way that Sage Intacct handles due-to/due-froms in the background,” Velazquez Maynard shares. She still reminds her accountants they don’t need to create these entries manually. “Sage does it for you. It handles it all for you. Just put it in and pay it and call it a day.”

Legacy created targeted dashboards for facility administrators, the people Velazquez Maynard describes as “on the front line every single day trying to run those buildings and running in circles.” These administrators now see their facility’s financial performance in real-time, allowing them to fix issues before month-end close.

The dashboards help administrators review accounts payable, correct miscategorized expenses, and monitor budgets as things happen, not after the fact.

The finance team itself is lean—just two main accountants (a senior and staff accountant), an AP team, and the executive leadership. This small team now manages complex financial operations that previously consumed far more resources.

Building an Integrated Tech Stack

Sage Intacct’s integration capabilities allowed Legacy to build a comprehensive financial ecosystem. They use SmartLynX for scheduling (critical when labor is their biggest expense), iSolved for payroll and HR, and Divvy for credit card management.

“What Sage Intacct does really well. is integrating with other software, and there is always some kind of solution that they can find you,” Velazquez Maynard notes. If Intacct doesn’t have what you need, “there’s someone out there that can team up with Sage and it can become part of the platform that will make you a winner.”

The Real Cost of Standing Still

When asked about advice for other healthcare finance professionals considering modernization, Velazquez Maynard is direct: “They can’t be afraid of the cost, because in all reality, the cost of not doing it is probably greater.”

She points to the hidden expenses of staying on legacy systems. “The hours that are going to be spent by your CFO, controller, and accountants trying to do manual things or in Excel that could be automatic—it’s going to end up paying for itself.”

For organizations worried about implementation complexity, Velazquez Maynard offers reassurance. The implementation partners “point you in the right direction. They tell you step by step what you need to do.”

Looking ahead, Legacy faces the same challenge Velazquez Maynard identifies as healthcare’s biggest issue: the labor force. “Finding good labor is hard,” she admits. The company regularly evaluates wage scales, trying to determine if higher pay will attract better talent or if they’re “just throwing money at something.”

With facilities sometimes forced to use agency staff at $55-65 per hour, having clear financial visibility through SmartLynX metrics helps them better control these costs. “You have to be staffed. So sometimes there’s just nothing you can do.”

Lessons for Healthcare Finance Leaders

Legacy’s transformation from 30 disconnected systems to a unified platform offers clear lessons for healthcare organizations. The speedy implementation proves that transformation doesn’t require years of disruption. The immediate benefits, from automated inter-entity transactions to real-time floor spending reports, demonstrate tangible returns on investment.

Most importantly, Velazquez Maynard’s experience shows that the right technology enables growth rather than just supporting operations. Legacy continues expanding, confident their financial infrastructure can scale alongside their ambitions. When Velazquez Maynard took the job, she told her boss, “If you’re planning on selling in the next 20 years, I am not taking this job.” With the foundation they’ve built, she might just keep that promise.

For healthcare finance professionals wondering if transformation is worth the effort, Velazquez Maynard’s journey provides a clear answer. The question isn’t whether you can afford to modernize; it’s whether you can afford not to.

Listen to the complete conversation with Velazquez Maynard on The Unofficial Sage Intacct Podcast to hear additional insights about managing multi-entity healthcare organizations, building effective financial teams, and navigating the unique challenges of the nursing home industry.

Will Intuit’s Push Upmarket Leave 30 Million Small Businesses Behind?

Earmark Team · January 16, 2026 ·

“This is the disconnect at Intuit Connect,” Blake Oliver observed during this episode of The Accounting Podcast. “They want to go up market, so they are talking with practice leaders at big firms. But their current customers are small firms and independent ProAdvisors. And that is why the vibe was not right.”

In this week’s episode, Blake and his co-host David Leary welcome Alicia Katz Pollock, host of the Unofficial QuickBooks Accountants Podcast, to unpack everything that happened at Intuit Connect 2025 in Las Vegas. Armed with 42 pages of notes, the trio discusses major changes coming to QuickBooks, including the new Intuit Accountant Suite that will replace QuickBooks Online Accountant by December 2026, widespread AI integration, and Intuit’s push to become an all-in-one platform competing with enterprise solutions.

A Conference Transformed

The atmosphere at Intuit Connect told the story before any keynote began. Alicia, who has attended every conference since its QuickBooks Connect days, noticed the dramatic shift immediately. “There were only a few dozen of us,” she said, referring to independent ProAdvisors who once filled the conference halls. Instead, she met “tons of first time attendees who were all employees at firms.”

David, who spent years at Intuit building the QuickBooks marketplace, remembered when the conference was “a celebration of accountants, bookkeepers and small businesses.” The company would display lists of ProAdvisors who’d been with them for years and give out ProAdvisor of the Year awards. “You used to get the chills because you’re like, I love all these people,” he recalled. “And now it’s like all about Intuit.”

Even the conference exit changed from cheerleaders with pom-poms to a drum corps, signaling a shift from celebration to something more corporate and impersonal. As Alicia put it, “They used to treat us like kings. This was much more about professional upskilling, like a normal conference.”

AI Everywhere—But Does It Work?

Intuit CEO Sasan Goodarzi’s keynote made the company’s direction clear. Seven years ago, they “bet the farm on AI,” and now the entire platform is moving in that direction. The promise sounds revolutionary: AI agents handling routine bookkeeping tasks, smart categorization, and automated workflows. The reality, according to users and the hosts, tells a different story.

David’s experience captures the frustration many feel. “Every time I go to the bank feed screen, my list of pending transactions just keeps going up,” he explained. Despite the promised AI agents, his unmatched transaction numbers keep climbing. “Nobody’s doing the work,” he said. To clear transactions, he had to manually fix broken connections from Expensify and reorganize how transactions were coded—exactly the kind of work AI was supposed to eliminate.

The hosts read a detailed email from a listener who outlined five critical problems with the forced AI rollout: miscategorized transactions, inaccurate reporting, bank feed errors creating double entries, a slower interface requiring more clicks, and most importantly, no ability to opt out. “I can’t get over my anger and frustration with this forced rollout,” she wrote, noting that she’s lost hours to troubleshooting instead of doing strategic work.

Alicia offered a more measured perspective, explaining that AI “still has to be trained” and needs to learn from each company’s specific patterns. “You have to give it one of everything,” she said, suggesting it might take “a quarter of data and probably a year” before the AI becomes accurate.

But David pushed back on this defense. “Intuit just spent $1 million on a conference and talked about how magical this is. Nobody said I need to train the agents. The marketing says it’s just going to do it.”

Blake offered a technical critique that cut to the heart of the problem. “AI is statistical and probabilistic and is not 100%,” he explained. Rather than replacing reliable rules with unpredictable AI, Intuit should “automate the creation of rules” that work accurately every time. He pointed to competitors like Ramp that use AI to create rules rather than replace them entirely.

The All-in-One Platform Play

Beyond AI, Intuit is transforming QuickBooks from an accounting platform that integrates with hundreds of apps into an all-in-one solution that does everything internally. The new features include integrated Mailchimp functionality, CRM tools, customer surveys, appointment booking, and marketing campaigns, all within QuickBooks.

During his keynote, Goodarzi made the strategy explicit: “You’ll pay less because you’ll need to pay for fewer apps.” This message, delivered while 75-80 third-party app vendors were exhibiting at the conference, created what David described as a “weird vibe.”

The hosts compared this approach to a multifunction printer. As Alicia explained, while it can print, copy, scan, and fax, “you’re not going to be able to put out a poster that you can put up on the wall.” Similarly, QuickBooks might do “a little bit of everything,” but businesses needing robust, specialized solutions may find themselves limited.

Blake expressed deeper concerns about this strategic shift. Having built a successful firm by combining specialized apps, he worries about the implications. “I know what happens when an app tries to do everything. It does everything, but it does it in kind of a mediocre way.”

The New Intuit Accountant Suite

One of the biggest announcements affects accountants directly: QuickBooks Online Accountant (QBOA) will be replaced by the Intuit Accountant Suite (IAS) by December 2026. 

The new suite will have three tiers. The free version will include all existing QBOA functionality. Two paid tiers (Core and Accelerate) will add new features like customizable dashboards showing KPIs across all clients, books review capabilities that let accountants fix issues without entering individual client files, and capacity management tools for firms.

“For the first year it’s going to be free because they have to develop it and design it and see if we like it,” Alicia explained. After that, some features will require payment.

The capacity management feature revealed another strategic shift. When firms reach capacity, the system will suggest hiring an “Intuit expert” or assigning clients to QuickBooks Live. As David observed, this essentially positions independent ProAdvisors as “labor for these bigger firms”—a fundamental change in how Intuit views its ProAdvisor community.

The Upmarket Push and Its Risks

The hosts identified a fundamental strategic risk in Intuit’s approach. By chasing an estimated 100,000 businesses that might need enterprise features, Intuit could leave “its flank exposed” to competitors targeting the tens of millions of small businesses needing simple, affordable solutions.

Evidence of this vulnerability is already emerging. Quicken, which Intuit spun off years ago, now offers business features for just $8 per month, compared to QuickBooks’ Simple Start at $38 monthly. New players like Digits offer free APIs to attract developers that Intuit’s ecosystem changes might alienate. Personal finance apps like Monarch Money are adding business features to capture the entry-level market.

“There are tens of millions of small businesses that don’t need enterprise features,” Blake argued. He shared how his firm succeeded by serving the low end of the market with streamlined, automated services at a few hundred dollars per month. “Sometimes it’s better not to try and compete with everybody in the same small pool and go to that bigger one that’s underserved.”

Alicia used a metaphor to describe the risk. Intuit has evolved from “a table with a single post in the middle of QuickBooks” to one with four legs including TurboTax, Mailchimp, and Credit Karma. But the QuickBooks leg was built on small businesses and their bookkeepers. “If that table leg collapses, the table’s going to fall over.”

Looking Forward

Despite the criticism, some developments show promise. Alicia highlighted genuinely useful features in development, including AI that considers industry context when categorizing transactions and dashboards that surface anomalies in client data. Intuit is also working on allowing users to create custom dashboard widgets using low-code tools, though David questioned whether this solves real business problems or just provides “fancier reporting.”

The conversation revealed a company at a crossroads. As Blake summarized, Intuit is building for “users who don’t yet exist while alienating those who made them successful.” The question is, as AI transforms accounting, will Intuit remember who they’re transforming it for?

For accounting professionals, whether these QuickBooks changes represent progress or problems depends largely on your firm’s size, client base, and willingness to adapt to Intuit’s vision of the future.

Listen to the full episode of The Accounting Podcast to hear all the details about product updates, pricing changes, and what these shifts mean for your practice. The conversation between three industry veterans who’ve watched QuickBooks evolve for over two decades offers warnings and opportunities for those paying attention.

Intuit Finally Tackles Practice Management But Will Accountants Actually Switch?

Earmark Team · January 9, 2026 ·

For years, QuickBooks Online Accountant (QBOA) served as little more than a client list with basic billing features. That’s about to change in a big way.

In episode 121 of The Unofficial QuickBooks Accountants Podcast, hosts Alicia Katz Pollock and Dan DeLong dive deep into everything they learned about Intuit Accountant Suite (IAS) at Intuit Connect. The hosts brought insights from their conversations with the developers and project managers building these new features.

Dan, who was one of the first four Intuit agents to support QBO back in 2013, found the transformation almost surreal. “To see its evolution from 2013, when it first started as just a client list dashboard to what it’s actually evolving into, is a pretty surreal thing,” he reflects.

Alicia spent most of the conference in what she calls the “Innovation Circle” rather than breakout sessions. In the Circle, she talked directly to developers at about 20 different stations, gathering pages of notes about features that will fundamentally change how accountants manage their practices.

From Simple List to Practice Command Center

The transformation starts with the news that Intuit Accountant Suite will replace QBOA entirely. The new home screen adapts to each user’s role and access level, making it different for everyone based on their specific workload.

“Instead of having to go into each of your clients and find out those anomalies, you’ll have a dashboard inside of a one-stop shop,” Dan explains. “You need to look into anomalies for this client, fix a disconnected account for this client, reconnect an app for that client. The dashboard basically lists the fires you need to put out today.”

The home screen will show integration issues across all clients, news with product updates, and a ProAdvisor team certification bar graph. You can pin custom items and see product recommendations, although Intuit promises these won’t advertise services you already offer.

One of the biggest workflow improvements is the new client groups feature. Instead of assigning permissions client by client and team member by team member, you can now create groups based on any dimension that makes sense, such as office location, industry, service type, or subscription level. Assign team members to a group once, designate a lead, and everyone gets appropriate access automatically.

This is especially valuable given the current wave of mergers and acquisitions in accounting. “With private equity happening in the accounting space and smaller bookkeepers joining forces to turn into larger firms, this was a big sticking point,” Alicia notes. The new realm consolidation features let you transfer clients between accounts and reassign primary admin status to accommodate these structural changes.

The Practice Management Play

Intuit Accountant Suite will have two different plans: Core and Accelerate. Core includes everything currently in QBOA and will remain free. Accelerate adds the new features and will have a price after the first free year. Some features, like Books Close, might be available à la carte.

Client Insights offers what many accountants have been building manually in spreadsheets. You’ll choose from over 30 KPIs at launch, with more coming. The dashboard refreshes every 24 hours, though you can update on demand. The AI “accounting agent” (shown as a sparkle icon) flags anomalies and significant changes across your entire client base.

“You’ll have default template views—P&L data, balance sheet data, bookkeeping data,” Alicia explains. “And then you’ll be able to design your own custom views as well, with your own KPIs.”

Books Close made Alicia do a double-take, as it works a lot like Double (formerly known as Keeper). The feature lets you handle routine reconciliation and review without clicking into individual client files.

The transaction review capabilities include counts for uncategorized transactions, transactions without payees, transactions posted to parent accounts, expenses without attachments, transactions over your threshold, transactions auto-added by bank rules, and transactions auto-posted by AI.

“That’s huge,” Dan responds to the bank rules visibility. “As long as you can do a batch action type of thing or multiple edits, that will actually put the word ‘quick’ back into QuickBooks.”

The workflow system assigns team members as preparer, reviewer, or approver. You create templates, assign them to new clients, and your month-end process is structured automatically. Capacity planning shows team workloads, tracks budgeted versus actual time, and lets you set utilization rates by person. When someone goes on vacation, you reallocate their tasks directly in the interface.

Intuit also positions QuickBooks Live experts as an overflow option when you’re over capacity—a feature that drew mixed reactions from the hosts.

Training Goes Firm-Wide

Jaclyn Anku, ProAdvisor Program Leader, explained to Alicia how they’re adapting to industry changes. “She’s really conscious that the industry is changing and the ProAdvisor program needs to stay relevant to today’s firms as we move into advisory and human intelligence,” Alicia notes.

The new training dashboard in IAS solves a persistent problem: every team member’s certifications lived in their own portal with no firm-wide visibility. Now administrators can view all staff certifications on one screen, track progress toward ProAdvisor tiers, access complete transcripts, assign courses firm-wide or individually, and set due dates with automated reminders.

The new CAS Foundation Badge indicates where Intuit sees the profession heading. It requires completing five programs, including a new three-hour AI for Accounting course, communication training, and financial analysis modules. Unlike regular certifications, there’s no test-out option. You must complete the training.

“It covers things you don’t get taught at accounting school,” Dan observes about the communication and soft skills components.

The resource hub adds marketing collateral, workflow templates, and presentation scripts for client trainings. Intuit commits to quarterly updates to keep screenshots and processes current.

What This Means for Your Practice

The hosts offer practical advice for navigating these changes. Since pricing isn’t available yet, they suggest testing features with one or two clients during the free year.

“Double does way more than this is going to do for any length of time,” Alicia notes realistically. “So if you’re only using the basic features of Double, then maybe this will work for you. But we don’t know the price, so we don’t know how it’s going to compare.”

“This is leveling up from individual details of having to go into each of your clients, or having to go into each of your staff members. It’s all in one place for you as a firm owner,” Dan says, summarizing the value proposition.

For solo practitioners or small firms without existing practice management tools, IAS offers infrastructure that was previously out of reach. For established firms with existing workflows, the calculation is more complex. You have a year to test, compare, and decide whether Intuit’s vision aligns with your practice needs.

It’s clear Intuit recognizes they were “leaving money on the table,” as Alicia puts it, and they’re moving aggressively to reclaim that territory. Whether they succeed depends on execution, pricing, and whether accountants find enough value to abandon their current tools.

Listen to the Full Episode

For the complete discussion including all the developer conversations and specific feature details, listen to The Unofficial QuickBooks Accountants Podcast. You’ll hear firsthand how these changes might impact your practice and get practical tips for making the most of the free trial period.


Alicia Katz Pollock’s Royalwise OWLS (On-Demand Web-based Learning Solutions) is the industry’s premier portal for top-notch QuickBooks Online training with CPE for accounting firms, bookkeepers, and small business owners. Visit Royalwise OWLS, where learning QBO is a HOOT!

Protect Your Bookkeeping Practice: Essential Boundaries That Preserve Your Value

Earmark Team · August 27, 2025 ·

When hosts Alicia Katz Pollock and Veronica Wasek spun their “Wheel of Rants” on a recent episode of The Unofficial QuickBooks Accountants Podcast, they landed on a topic that sparked an energetic discussion: “The 20 things that accountants should never do.”

What followed was a candid conversation about the essential boundaries every bookkeeper should establish to protect themselves and their clients. Whether you’re just starting your bookkeeping practice or you’re a seasoned professional, these boundaries are critical safeguards for building a sustainable business.

Client Relationship Boundaries: Who’s Really in Charge?

“Allowing clients to control the work we do and really treating us as employees” topped Wasek’s list of boundary violations. She explained that many bookkeepers, especially those transitioning from employee roles, fall into the trap of letting clients direct their work.

“The client shouldn’t be directing the work you do,” Wasek emphasized. “There should be proper diagnosis done by us as accountants and then we give the client our recommendations.”

This distinction is crucial: Are you following orders or leading the process? As Katz Pollock  pointed out, “If you’re a bookkeeper with your own firm or your own practice, you should be the one guiding the narrative.” Otherwise, you might actually be functioning as an employee rather than an independent contractor.

Financial Boundaries: Know Your Worth

Both hosts shared strong opinions about working for free or undervaluing services. Wasek explained how offering free work “devalues our industry as a whole” and signals that you don’t value your own expertise.

Katz Pollock added a practical concern: “If you were willing to do it for free, why would I pay you $500 a month to do it?” This initial boundary violation creates expectations that become nearly impossible to reset later.

Another common mistake is marking down invoices without discussion. Wasek shared an example based on her own experience. “My fee was $10,000 based on all the time that I spent on it, but I don’t think they’re going to pay me $10,000, so I just charge them $5,000.”

She now recognizes this as a serious boundary violation, explaining, “We tend to project our own feelings about money to our clients.” Instead of assuming clients won’t pay, have an open conversation about pricing.

Katz Pollock offered a practical strategy for those who bill hourly. “I charge what I consider a reasonably high rate, and that allows me to give a discount. Then I feel like everybody wins. I’m still getting a satisfactory rate, and they feel good.”

The hosts also warned against becoming financially dependent on just a few clients. “What if one out of those three leaves and you were financially dependent on that client?” Wasek cautioned. This dependency traps bookkeepers in problematic relationships where they can’t enforce other boundaries for fear of losing essential income.

Security Boundaries: Protecting Your Clients and Yourself

“Having direct access to the client’s bank accounts or their bill payment” is a practice Wasek strongly discourages. She shared a sobering example of a client that embezzled $8 million through their in-house bookkeeper, who had unrestricted access.

Katz Pollock acknowledged the practical challenges, noting she sometimes needs bank account access to view statements or check images. Her solution involves strict controls: “We have a 1Password vault that nobody has access to except for me and my contracted bookkeeper,” plus explicit language in her engagement letter that they “will never take any action either on your behalf or at your request.”

Both hosts emphasized the importance of secure password management. “Nowadays, you need to have unique passwords for everything,” Wasek explained, recommending systems that limit credential visibility to only those who absolutely need them.

Email communication presents another security concern. “The bane of my existence is emails,” Katz Pollock admitted, noting important client communications often get buried. More critically, Wasek warned, “There are so many email scams going on right now where you think you’re talking to your client and they are not your client.”

She shared a chilling example: “One of my clients was a victim of an email scam with a vendor. He sent a couple of million dollars to this fraudulent vendor, and then couldn’t do anything about it.” This led her firm to abandon email entirely for client communications, moving to secure platforms instead.

Professional Expertise Boundaries: Know Your Limits

“Taking a client when you lack the required skills” and giving legal or tax advice without proper qualifications made both hosts’ lists of major boundary violations.

“Certain industries and certain types of clients are more complex,” Wasek explained, highlighting areas like e-commerce and nonprofit accounting that require specialized knowledge.

Both hosts stressed that bookkeepers should never give tax or legal advice without proper credentials. “If you don’t have a law degree and if you don’t have a tax designation, then you can’t actually back up and stand by the advice you’re giving,” Katz Pollock cautioned.

Instead, they recommended developing relationships with specialists and having prepared responses for common client questions. As Wasek suggested, “I would try to give them the right words to use to ask their CPA the proper question.”

Documentation Boundaries: Get It in Writing

“Not using engagement letters” was another boundary violation, both hosts emphasized. Wasek learned this lesson “the hard way” after initially “working on a handshake,” explaining that formal agreements “really set the tone for the entire relationship.”

A comprehensive engagement letter should outline services provided, responsibilities, pricing, payment terms, and procedures for ending the relationship. Katz Pollock recommended reviewing engagement letters annually. “I look to see if their scope has changed. How many checking accounts did I agree to and how many do they have now?” This gives a “tangible reason for raising our prices” beyond just annual increases.

Both hosts also advocated for paid diagnostic assessments before committing to new clients. This smaller initial engagement helps evaluate a client’s responsiveness and complexity before making longer-term commitments.

Personal Boundaries: Protecting Your Time and Energy

The hosts discussed the common issue of bookkeepers acting as “unpaid therapists” for their clients. Wasek recalled a client who “would keep me on for at least an hour” multiple times weekly, making it impossible to complete actual work. She learned to establish time parameters, saying, “I’d love to talk to you, but I have a meeting in 15 minutes.”

Another crucial personal boundary involves maintaining client confidentiality. “You never, ever, ever talk badly about either the business owner or a bookkeeper to another business owner or another bookkeeper,” Katz Pollock stressed. This includes avoiding sharing information between clients or discussing former clients with their new bookkeepers without explicit permission.

Wasek shared a situation involving partnership conflicts: “I had to terminate the relationship. I would rather this client think badly of me for leaving them without a bookkeeper than to attack the other partner or to tattletale.”

Building a Stronger Practice Through Boundaries

Throughout their discussion, Wasek and Katz Pollock emphasized that proper boundaries ultimately create more sustainable and rewarding businesses.

“I am a big believer in karma, and that when one door closes, another one opens,” Katz Pollock shared. “If you have a really large client that you depend on, and either they let you go or you just find it toxic, I don’t recommend staying.”

Wasek agreed, adding that when bookkeepers release problematic clients, they gain “so much more mental energy to devote to better clients.”

For bookkeepers looking to establish stronger boundaries, the hosts recommended:

  • Getting proper training to understand your expertise and limitations
  • Using engagement letters reviewed by legal professionals
  • Implementing secure technology solutions for passwords and communications
  • Developing scripts for common boundary challenges
  • Building relationships with specialists for referrals
  • Conducting paid diagnostic assessments before committing to new clients

As Katz Pollock concluded about maintaining professional boundaries, “It says way more about you than it does about them.” It’s a reminder that how you establish and maintain boundaries ultimately defines your professional reputation and the health of your practice.

To hear more detailed insights about these essential bookkeeping boundaries, listen to the full episode using the player below or wherever you get your podcasts.


Alicia Katz Pollock’s Royalwise OWLS (On-Demand Web-based Learning Solutions) is the industry’s premier portal for top-notch QuickBooks Online training with CPE for accounting firms, bookkeepers, and small business owners. Visit Royalwise OWLS, where learning QBO is a HOOT!

When Two Accounting Apps Listen to Their Customers (And Actually Do Something About It)

Earmark Team · July 22, 2025 ·

Picture this: It’s 2021 at ‘Appy Camp, and Ben Stein from Keeper is standing at a bar, drink ticket in hand, ready to exchange it for a well-deserved cocktail after a long day of conference sessions. But when Alicia Katz Pollock rushes past—bass guitar case slung over her shoulder, racing to join the evening’s music circle around the fire—and tosses him her drink ticket with a hurried “Can you get me my drink?”, Ben doesn’t hesitate. He heads to the bar, discovers they’re not accepting drink tickets, and simply buys her a drink anyway.

That spirit of going above and beyond would prove fitting. Three years later, Ben’s company, Keeper, just launched an integration with Anchor that’s making accounting professionals everywhere take notice. When Katz Pollock brought together Stein and Tal Ben Bassat from Anchor for a special episode of The Unofficial QuickBooks Accountants Podcast, the conversation revealed how real software partnerships actually happen.

The story isn’t about corporate strategy meetings or market research. It’s about two companies that actually listened when their customers said, “We want these apps to work together.” And then they did something most software companies don’t: they made it happen…

…like chocolate and peanut butter…better together!

When Customers Become Your Product Team

Here’s what most software companies get wrong: they build features based on internal roadmaps instead of user requests. But when Stein’s team at Keeper and Ben Bassat’s team at Anchor started getting the same message from customers, both companies did something simple. They listened.

“Really, the idea came from our mutual customers,” Ben explains. “This is something that our customers asked for and Anchor’s customers asked for. We have a lot of overlapping customers and we want to keep them happy.”

Ben Bassat’s approach at Anchor takes this customer focus even further. “Everything we do on Anchor comes from our clients. Every feature, every development we have,” he says. “Our product team spends full days speaking to customers about what they need.”

The proof came after they launched. Stein admits it “caught my team off guard” with the response. “We go live with the integration, and all of a sudden, our support team was just inundated with dozens of tickets from Anchor customers and Keeper customers that were super excited about getting this up and running.”

This customer-driven approach creates a simple but powerful advantage: when your users tell you exactly what they need to work more efficiently, you don’t have to guess what to build next.

How the Integration Actually Works

For those not familiar with these tools, here’s what they do.

Anchor handles contracting and billing. Accountants can create proposals with multiple pricing tiers, get electronic signatures, and automatically invoice clients monthly. The invoices sync to QuickBooks Online. Keeper manages your bookkeeping workflows and checklists. It integrates with QBO so you can review transactions, ask client questions, and track your monthly procedures without jumping between systems.

Now here’s where the integration gets useful. When a client receives a proposal in Anchor, they can choose from different service packages and even agree to automatic annual price increases. Once they sign and connect payment information, the integration takes over automatically.

Based on your Anchor settings, the system auto-configures a client in Keeper, applying templates, creating tasks, and setting properties—all without manual work. “Once the client signs the agreement, Anchor will take the upfront payments. So you’re already clear on that. And then your team gets a notification and they start to work on Keeper immediately,” Ben Bassat explains.

This eliminates what Ben Bassat calls the traditional approach: “someone in your back office who starts organizing the onboarding process.” No more Excel spreadsheets tracking tasks. No more manual emails. No more wondering where each client stands in the pipeline.

Future updates will include amendment management. When you add services in Anchor, it will automatically trigger new workflows in Keeper. The integration keeps evolving based on what users really need.

Why Specialized Tools Beat All-in-One Platforms

Both companies made a conscious choice to focus on what they do best rather than trying to build everything. “No one can do everything perfectly. It’s not possible,” Ben Bassat explains.

His philosophy is clear: master your core function, then integrate with others who’ve mastered theirs. “Our approach on Anchor is not to give people a half-baked CRM experience or half-baked project management or practice management experience because it will not be as good. Keeper spent years developing their product.”

Stein agrees, recognizing that building billing software is “enormously complex.” Meanwhile, Keeper has spent years perfecting practice management and client communications that are “so deeply coupled to each other” that splitting them across multiple systems would create problems.

As Katz Pollock puts it, QuickBooks Online is like “a multifunction printer where it can print and it can copy and it can fax, but it doesn’t do any of them really, really well.” That’s why we have an entire ecosystem of specialized apps that excel at their one thing, and then connect to create something more powerful than any single platform.

Building the Integration Right

This wasn’t just two companies slapping together a quick connection. It was Keeper’s first major integration, and both teams approached it with their full attention.

“It surprised me how involved it was,” Stein reflects. “Anchor sort of took the whole process very seriously.” Keeper had to modify their API and release new endpoints specifically to support what Anchor needed.

Ben Bassat’s team matched that commitment. “Our approach is to deliver the best we can.” The development included extensive customer research, with Anchor’s product team speaking directly to Keeper users to understand their expectations.

The mutual respect between companies is evident in how they talk about each other. Stein praises Anchor’s authentic customer approach, while Ben Bassat marvels at Keeper’s user loyalty: “Clients are in love with the company, with the product. It’s something you don’t see a lot.”

When both companies share the same standards for quality, the collaboration works better.

The Bigger Picture

The Keeper-Anchor integration is a model for how accounting technology should evolve. When specialized companies listen to their customers and collaborate instead of competing, they create something more powerful than bloated platforms trying to do everything poorly.

The overwhelming user response—support teams flooded with excited customers wanting immediate access—shows that accountants recognize good tools that work together seamlessly. You don’t need another platform that does everything adequately. You need best-in-class solutions that communicate perfectly.

As these founders envision a future with universal bank APIs and seamless connectivity between all accounting apps, they’re describing an ecosystem where your software works as hard as you do. Where signing a proposal automatically sets up workflows, amendments in one system update tasks in another, and tools anticipate needs instead of creating more work.

When software companies prioritize partnership over competition and specialization over generalization, everyone wins. Your clients get better service. Your team gets better tools. And you get back to what you do best: serving clients instead of wrestling with software.

Want to hear the full conversation? Listen to this episode to discover how customer feedback drove this integration, what’s coming next, and why the future of accounting technology is specialized, connected, and customer-driven.


Alicia Katz Pollock’s Royalwise OWLS (On-Demand Web-based Learning Solutions) is the industry’s premier portal for top-notch QuickBooks Online training with CPE for accounting firms, bookkeepers, and small business owners. Visit Royalwise OWLS, where learning QBO is a HOOT! Click on the following links if you want to learn more about Keeper and Anchor.

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