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From Homeless to $20 Billion Deals: An Accountant’s Journey Through Automation

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Fifteen years ago, Devon Coombs was sleeping in his car. Skip ahead, and he’s helping negotiate $20 billion AI deals at Google Cloud. His story isn’t just another rags-to-riches tale—it’s a preview of accounting’s future.

I interviewed Devon on the Earmark Podcast, and what struck me wasn’t his remarkable turnaround. It was his pattern recognition. Devon lived through technology’s destruction of the music industry. Now he’s watching the same forces reshape accounting. The difference? This time, he’s riding the wave instead of getting crushed.

The Recording Studio That Technology Killed

At 18, Devon owned Antipop Records in North Hollywood. He’d grown up in foster care. His mother died when he was 15, and he never met his father. But he had talent and a passion for music, so he did what passionate people do: invested everything in professional recording equipment.

Then Logic Pro happened.

“My rates went from $50-100 an hour to competing with guys charging ten bucks,” Devon told me. “Musicians could record in their kitchen and get 90% of my quality.”

The 2007 recession started the bleeding. Technology finished it. Devon’s $100,000 studio became worthless overnight. He ended up homeless, sleeping in his car, trying to figure out what went wrong.

Here’s what he learned: Technology doesn’t destroy industries. It destroys intermediaries. Musicians who could compose, produce, and distribute music thrived with infinite digital instruments at their fingertips. Recording engineers and session musicians who only executed other people’s visions? They became extinct.

The Community College Revelation

While living in his car, Devon started taking business classes at Pierce College, a community college in the San Fernando Valley. He planned to become a music attorney. But accounting grabbed him instead.

“I was surprised by how much I liked doing the work,” he says. The profession also offered something Devon had never experienced: predictable career progression and financial security.

His first internship taught him an unexpected lesson. The CPA who hired him was successful despite being disorganized and barely keeping clients happy. “If this guy could make bank being this scattered,” Devon thought, “imagine what I could do if I actually tried.”

1,000 Cold Calls and One Big Bet

At Deloitte, first-year associates reconcile bank statements. Devon had other plans. He made 1,000 cold calls and emails to controllers across Los Angeles.

His pitch was brilliant in its honesty: “I’m new at Deloitte. I want to learn. Give me your time, and I promise you’ll get more attention from me than from any partner here.”

It worked. He landed GoGuardian as a client—one of the first ASC 606 implementations in the country. The partner told him it would never work. Nobody wins clients as a first-year associate.

Deloitte gave Devon a $100 bonus for bringing in a $100,000 client. That’s when he knew the Big Four model wasn’t for him. When Effectus Group offered to double his salary plus commission, he jumped.

Becoming the 606 Expert

ASC 606 was rolling out, and nobody understood it. The guidance ran thousands of pages. Most accountants waited for CPE courses to explain it.

Devon printed every page.

“I’d read 30 pages every night, then figure out how to apply it,” he explained. In two years, he completed over ten implementations across industries—software companies, call centers, and even nonprofits.

Six months into his new job, he won Automation Anywhere as a client. A multibillion-dollar unicorn choosing a boutique firm over the Big Four. Why? Because Devon knew 606 better than anyone.

“Put in six months of deep work on any technical topic,” he told me, “and you’ll blow everyone else out of the water.”

The AI Orchestrator Revolution

Today, at Google Cloud, Devon helps negotiate billion-dollar AI deals. But here’s what matters: He’s not just selling AI. He’s living the future of professional services.

“Agentic workflows,” he calls them. AI bots handle routine tasks while humans orchestrate the work. “You’ll have bots calling companies, and no one will know they’re bots. All those little tasks in between? Just bots talking to each other.”

It’s the music industry all over again. Technology eliminates executors and elevates orchestrators. The accountants who only know how to follow procedures? They’re the session musicians of the 2010s. The ones who can design systems, manage AI workflows, and apply judgment? They’re the producers.

Devon is now leaving Google for PCG (Principal Consulting Group), where he’ll build a practice around this orchestrator model. His goal: “better quality work with higher judgment applied with all my expertise and one-tenth the cost.”

Your Window Is Closing

Recording studios were given years of warning, but they ignored it. By the time musicians started canceling sessions, the game was over.

Accounting firms today are experiencing the same warning signs: clients questioning fees, staff leaving for tech companies, and AI tools handling basic bookkeeping. The script is playing out again.

But unlike Devon’s recording studio, we can see it coming. We can choose to be orchestrators instead of executors. We can build practices around AI enhancement instead of human grinding.

The transformation isn’t some distant future. Devon’s already building it. He’s creating an entirely new service model where CPAs orchestrate AI agents to deliver superior results at a fraction of traditional costs.

“The AI movement is our chance to add real value,” Devon insists. “But only if we lean in now.”

Listen to the full episode to understand how to position yourself for this shift. Because Devon’s journey proves one thing: Those who embrace disruption don’t just survive. They discover possibilities they never imagined existed.

The question isn’t whether AI will transform accounting. It’s whether you’ll be the orchestrator or become obsolete. Devon made his choice. What’s yours?

Avalara Tax Research: The Answer to Your Clients’ Toughest Sales Tax Questions

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“Is this service taxable?” It’s a seemingly simple client question that can send accountants down a rabbit hole of research, often leading to uncertain Google searches and hours navigating complex state websites.

“Google’s great for some things, but when it comes to figuring out the taxability of products, it is lacking,” explains Blake Oliver in a recent Earmark Expo webinar. “As anyone who has worked with sales tax questions knows, the answers are different by state and by local jurisdiction. It’s a giant mess.”

Sales tax isn’t something most CPAs learn in school, making these questions particularly challenging. Many accountants refer clients to specialists when they can’t find reliable answers quickly enough.

In the webinar, Luke Marlatt from Avalara demonstrated how their Tax Research tool helps accountants tackle these challenges confidently. Let’s explore what makes this solution work and how it could benefit your practice.

How Avalara Gathers and Organizes Tax Information

Behind Avalara’s platform is an impressive research operation that transforms chaotic multi-jurisdictional tax laws into accessible, actionable information.

“We employ a gigantic team of researchers who spend all day, every day going to find information,” Marlatt explains. “We’re scrubbing over 27,000 web pages every single day. That’s not just some poor intern in the basement clicking on web pages; they have web crawlers and all this kind of cool technology.”

What sets Avalara apart is what happens after data collection. Real human experts verify every piece of information, translate complex tax code into plain language, and track changes down to case law and local regulations.

The team’s commitment goes beyond passive monitoring. When necessary, they actively chase down information through direct outreach to tax authorities. Marlatt shared how one colleague spent 2.5 hours on the phone with tax authorities in Jackson, Wyoming, to confirm a customer’s tax rate question.

This thorough approach has earned such credibility that Colorado, Missouri, and the Alaska Municipal League actually use Avalara’s data to power their own public-facing websites. 

Key Features That Make Research Easier

The webinar demonstration highlighted several standout features designed to make sales tax research more efficient and user-friendly:

Simplified Nexus Determination

Rather than forcing users to interpret complex legal language, Avalara converts nexus requirements into straightforward yes/no questions.

“Instead of reading through the law trying to figure out what they mean—which in Washington, you’d have to read through five totally different parts of the revenue code—we just turn them into yes/no questions,” Marlatt explains.

This makes it easy to interview clients who might not understand tax terminology but can answer simple questions about their business activities.

Multi-State Comparison

With a single click of the “compare” button, users can apply a tax question across all states simultaneously, eliminating the need to research each jurisdiction individually.

“You hit the compare button and literally have your answer in every single state in the country,” Marlatt demonstrates. “Then you can hit this export button to dump it into Excel and start a workbook for a Nexus study.”

Customizable Tax Matrices

The Tax Matrix feature allows you to create customized, multi-state, multi-product matrices showing tax liability across different jurisdictions. You can save these matrices in the system and they’ll update automatically whenever relevant tax laws change.

“If you provide a tax matrix to your client, they’re going to want it updated. And traditionally that’s a difficult thing,” Marlatt explains. With Avalara, “The only thing you need to do is log in and hit the export button. And you’ve now got an updated tax matrix for your client.”

This creates an opportunity for subscription-based services, as Leary pointed out during the webinar: “And you build a quarterly tax research update into your fees.”

Precise Rate Lookups

The platform includes rooftop-level tax rate lookups, allowing users to find exact rates for specific addresses. The system shows the breakdown of rates by jurisdiction, essential for places like California where returns require this detail.

An interactive map displays the exact boundaries of taxing jurisdictions, making it easier to visualize where different rates apply.

Change Tracking and Updates

Users can toggle on a “highlight changes” feature that visually marks modified content with color indicators. This helps accountants quickly identify what’s changed since their last review.

The customizable email update system notifies you about tax changes daily, weekly, or monthly, filtered by content areas and specific states. These updates provide both an overview and detailed information about specific changes.

Marlatt shared how this helps catch significant changes: “The state of Kentucky defines SaaS as a service—they changed their law at the beginning of 2023. Because of that service law change, SaaS is now taxable in Kentucky as well.”

Expert Research Assistance

When questions arise that users can’t resolve through self-service research, the “Contact a Tax Expert” function connects them with Avalara’s team of expert researchers (mostly attorneys).

“Ninety four percent of the time, we beat our 24-hour mark and 71% of the time we actually beat the hour mark,” Marlatt notes regarding their response times. Last year, the team answered approximately 8,900 questions.

Avalara Tax Research also saves previous Q&A exchanges in a searchable repository, allowing users to benefit from questions other customers have asked.

Accessible for Firms of All Sizes

While these capabilities might seem designed for large firms, Avalara Tax Research serves accounting practices of all sizes.

“We have all the big four and most of the really big firms across the country using our tax research. We have mom and pop shops,” explains Marlatt. “Most of the demos I do are for single person operations with two or three people in a firm.”

For firms concerned about audit protection, Avalara offers an audit information guarantee. While they don’t provide direct tax advice or audit defense (leaving that advisory role to accounting partners), they stand behind their information’s accuracy.

“We will back up our information under audit directly with that auditor,” Marlatt explains. “We will go and defend that information with the auditor. We say, ‘Here’s all our research. Here’s how we got from A to B.'”

The platform also includes training resources to help firms maximize their return on investment. “There’s a team of trainers that make sure you get the most out of this tool,” Marlatt notes.

Adding a Valuable Service to Your Practice

Avalara Tax Research helps transform a persistent challenge into a strategic advantage. By providing authoritative answers to sales tax questions, firms can build service offerings around tax compliance while delivering more value to clients.

When clients receive clear, authoritative answers instead of tentative responses or referrals to specialists, it strengthens their trust in your firm. When you can proactively alert them to regulatory changes before they become compliance issues, you position yourself as a true advisor.

For practitioners who want to see these capabilities in action, watch the on-demand webinar. Tax complexity continues to increase, and having reliable resources to navigate this landscape is essential for serving clients effectively.

Women in Accounting Need Mentors Who See Their Potential Before They Do

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“We see in others what we fail to see in ourselves.”

This simple but powerful insight came from a coffee conversation between two accounting colleagues. One was sharing her frustrations about advancing in a male-dominated leadership environment. The other pointed out strengths that were completely invisible to their owner: clear communication, authentic presence, and natural insight.

This conversation sparked a recent episode of the She Counts podcast, where hosts Questian Telka and Nancy McClelland dive into why mentorship is critical for women in accounting.

The Hidden Crisis in Accounting Leadership

The numbers tell a troubling story. Men and women enter the accounting profession at roughly equal rates: about 50/50. But women hold only 19% of partner positions in CPA firms nationwide. 

As Nancy points out, some major accounting firms are completely scrapping their diversity, equity, and inclusion programs (while others are doubling down on them). “Think about what the future of leadership in those companies is going to look like,” she says.

The reality is that this leadership gap isn’t about qualifications. When Questian worked at a Big Four firm early in her career, seeing a female chairperson of the board felt “unbelievable,” not because the woman wasn’t qualified, but because such representation was so rare.

Even more troubling are the explicit barriers that still exist. One colleague shared how she was promised a partner position when she joined a firm. After years of working toward that goal, the position went to a male colleague instead. When she had her first child, firm leadership told her she “wouldn’t want to be in a leadership role now anyway, because she was a mom.”

This kind of thinking—illegal as it is—shows the deeper assumptions that still limit women’s advancement.

Civil rights leader Marian Wright Edelman said it best: “You can’t be what you can’t see.” When leadership representation is so skewed, it creates a visibility problem. Women entering the profession may limit their own ambitions simply because they haven’t seen enough examples of women successfully reaching senior leadership roles.

The Science Behind Seeing Potential

The power of mentorship isn’t mysterious; it’s grounded in neuroscience that explains why outside perspective can literally change how we see ourselves.

As women, we’re often taught to fixate on our shortcomings rather than our strengths. “It is so common for us to focus on looking at our negatives,” Questian explains, “that we are often not paying enough attention to what our good traits are, and all of the positives that we bring to the table.”

Nancy admits she struggles with this, too. “If I’m naturally good at something, I don’t really take credit for it. I don’t think there’s anything impressive about this. It just is.”

This is where the science gets fascinating. Mirror neurons make it possible for us to learn something without doing it ourselves. When we watch someone teaching on stage or demonstrating a skill, “the audience can actually learn that thing as if they were doing it themselves,” Nancy explains.

In mentorship relationships, this means we can observe behaviors in our mentors and begin to see those possibilities for ourselves. When Nancy saw women like Claudia Hill speaking at accounting conferences, her immediate reaction was “me too. That’s a thing I’d like to do.”

When we receive positive feedback from someone we trust, our brains release dopamine. This reinforces the behavior that created the praise in the first place. “Getting a positive affirmation from it makes you much more inclined to continue to repeat it,” Questian says.

This creates a positive cycle where confidence builds on itself, leading to more confident behaviors that generate more positive responses.

This science helps explain Questian’s remarkable transformation. She went from someone who “could hardly get on a zoom call” to confidently delivering webinars and speaking at conferences. When Nancy pushed her to take a Theater of Public Speaking class, she wasn’t just suggesting skill-building; she was recommending a way to rewire her brain around public speaking anxiety.

Even today, Nancy provides the outside perspective that catches limiting thoughts before they take hold. When Questian says something like, “I’m going to submit this topic to Intuit Connect, but I’m sure they won’t take it,” Nancy immediately calls it out: “Is that your lizard-brain trying to protect you from rejection?”

Finding Your Mentors

Understanding the science is one thing. Actually building these relationships is another. The good news is that mentorship opportunities exist everywhere… if you know where to look.

But first, you need to get clear about what you actually need. As mentor Gaynor Meilke told Nancy, “How are you going to get to where you want to be if you don’t know what that is?”

Sometimes you need technical guidance. Sometimes confidence building. Sometimes a roadmap for advancement. Sometimes just someone who understands your challenges.

Questian never had a formal mentorship program. Instead, she’s found value in informal relationships with people who share similar values and communication styles.

Conferences are gold mines for mentorship connections. Both hosts trace pivotal moments to conference encounters. LinkedIn, Facebook groups, mastermind communities, and even your current workplace all offer potential mentor relationships.

The step that stops many people is actually asking for help. “You have to ask them,” Questian emphasizes. “What’s the worst they can say? No.”

Questian learned this when she persistently pursued Nancy as a mentor, even after initial hesitation. Sometimes the answer is no. But often, people who seem unreachable are willing to help if you show genuine interest.

Mentorship doesn’t depend on traditional hierarchies either. Nancy’s relationship with Melissa Miller Furgeson shows peer mentorship in action. “I feel so comfortable being able to go to her and say, I have no clue what I’m doing, and she’ll be like, here’s a Loom.”

Questian notes that mentors can even be younger than you. She considers Krista Marina Apardian from Theater of Public Speaking a mentor despite Apardian being younger, recognizing her as “an incredible speaker” with valuable expertise.

Different life phases need different types of mentorship. When Nancy needed encouragement to pursue tax preparation, Theresa Briggs saw potential Nancy couldn’t recognize. She gave Nancy a CCH Master Tax Guide with an inspirational inscription Nancy still treasures.

When Nancy needed business operation skills, Clare Karchmar taught her to “come to me with solutions, not problems.” This lesson fundamentally changed how Nancy approached professional challenges. Karchmar even gave Nancy a name badge that said “Hello, I’m: Shocked” to help break the habit of expressing surprise instead of focusing on solutions.

Recognizing Bad Mentorship

Not all mentorship relationships are helpful. Recognizing warning signs protects you from relationships that could harm your career.

Nancy shares a cautionary tale about approaching a leader for help with overwhelming work challenges. The leader’s solution was to make herbal tea and suggested yoga. “That would not have happened to a man.”

Warning signs include mentors who seem more interested in making themselves look good than developing you; those who take credit for your work; or anyone whose treatment feels patronizing.

Nancy advises, “If something happens that would never happen to a man… this is not your person.”

Being a Mentor Yourself

The mentorship relationship works both ways. Even as Nancy mentors Questian, she continues seeking mentorship for her own challenges.

“I am going to be turning 53 years old in a couple of days, and I am still in need of mentorship,” Nancy says. “We need to both have and be mentors at every stage of our lives.”

This eliminates the pressure to wait until you’re “qualified enough” to help others. Your current struggles and experiences are valuable to someone a few steps behind you in that area of life.

Some women hesitate to mentor because of imposter syndrome. “What do I have to offer?” is a common thought. But as Nancy points out, “Sometimes it’s your mistakes and your failures and your experiences that make you a more valuable mentor.”

When women support each other through mentorship, they create visibility that makes ambition feel achievable for the next generation. This gradually shifts from initially seeing a female leader as “unbelievable” to it eventually feeling normal.

Moving Forward

The accounting profession’s leadership gender gap at least partially stems from the absence of mentors who can see and nurture potential before women recognize it themselves.

As Marianne Williamson reminds us, “When you let your light shine, you unconsciously give others permission to do the same.”

Building mentorship relationships is about creating the visibility and support systems that will help other women recognize and develop their potential, too.

Listen to the full episode and join the conversation on the She Counts Podcast LinkedIn page. The hosts want to know how firms and businesses can build good mentorship cultures and what mentorship experiences have worked for you. Share your thoughts and experiences to help build a stronger community of women supporting women in accounting.

Whether you’re seeking mentorship or stepping up to mentor someone else, remember that these relationships have the power to transform the profession. The accounting industry’s future depends on women supporting women, and that future starts with the mentorship relationships we build today.

How Growing Businesses Can Automate and Protect Payments

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For finance teams, finding the right bill pay solution can feel like Goldilocks searching for the perfect porridge—many options are either too basic for complex operations or too sophisticated and expensive for mid-market needs. 

At a recent Earmark Expo webinar, hosts Blake Oliver and David Leary invited Omri Mor from Routable to demonstrate how their platform fills this critical gap in the accounts payable market.

“Either the bill pay app is too big for your client, or it’s too small for your client. Sometimes it’s just never the right size,” explained David when introducing the session. “That’s the struggle we have as accountants—getting the right bill pay app for clients.”

When It’s Time to Graduate from Basic Bill Pay

Routable positions itself as the logical next step for businesses that have outgrown basic bill pay solutions but aren’t ready for complex enterprise systems. According to Omri, the platform serves businesses processing anywhere from 100 to over 100,000 payments per month.

“We typically recommend considering a graduation from Bill.com at about 100 to 250 bill payments per month,”  explained. He outlined seven indications that it’s time to upgrade:

  1. Transaction volume exceeding 100 monthly payments
  2. Need for better ERP synchronization (Routable boasts a 99.8% sync success rate)
  3. Multi-entity support requirements (from 2 to 85+ entities)
  4. Complex approval rules based on different business dimensions
  5. Delegation requirements across growing finance teams
  6. Subsidiary management complexity
  7. Improved data integrity needs

Perhaps most importantly, Routable doesn’t require businesses to replace their existing accounting systems. As David highlighted during the demo, “If you’re on QuickBooks or Xero, that’s your GL, and you grow to a point, you can just add on Routable. You don’t have to go get a whole new ERP and replace your whole system.”

Powerful Features That Grow With Your Business

The demonstration showcased several standout features that address common pain points for growing businesses:

Seamless Vendor Management

Routable offers a branded vendor portal that doesn’t confuse vendors with third-party interfaces. “We don’t want to hijack your vendor. We don’t want to market to your vendor. We don’t want to confuse your vendor,” Omri emphasized.

The custom-branded portal allows vendors to self-onboard by providing contact information, completing tax forms electronically, and securely connecting bank accounts. The platform also includes built-in 1099 management, eliminating the need for separate tax filing software.

Deep ERP Integration

One of Routable’s most impressive capabilities is its real-time integration with accounting systems such as Oracle NetSuite and Sage Intacct. The platform automatically pulls all fields from your ERP—including custom fields—without additional setup.

“Let’s say you remove class, we’ll remove class. Let’s say you add a new field called ‘David’s favorite ice cream.’ we load ‘David’s favorite ice cream,'” Omri explained. This adaptability ensures the system always reflects your current accounting structure.

Flexible Approval Workflows

The platform allows highly customized, multi-level approval rules based on any field in your ERP system. You can nest rules within other rules for maximum flexibility, and approvers can respond directly via email without logging in.

“Choose your own adventure. It’s one of the most important things we’ve found in accounting and finance,” Omri noted.

Advanced Purchase Order Matching

For inventory-backed businesses, Routable offers sophisticated two-way and three-way matching capabilities. The system supports up to three million SKUs and can process thousands of invoices with detailed line items within seconds.

“This process would take 25 to 30 minutes for a human to do. We’re doing this within split seconds, and we’re coding it for you,” Omri highlighted.

Fighting Fraud with AI

Perhaps the most forward-thinking aspect of Routable’s platform is its upcoming AI-powered fraud detection system. This feature addresses a critical problem: mid-market companies lose an average of $280,000 annually to invoice fraud.

“Not only is faking invoices and receipts here, but faking phone calls is here,” Omri explained. “I can build an agent that sounds exactly like a human today and confirm [incorrect banking details]. So our old methods are not enough… we want to fight AI with AI.”

The system automatically flags suspicious elements in invoices, paired with confidence scoring, including:

  • Modified text in vendor names, dates, and amounts
  • Address changes from previous invoices
  • Duplicate invoice numbers
  • New or changed bank account details
  • Mismatches between stated banks and routing numbers

Omri shared a real-world example where Routable helped prevent a sophisticated $1 million fraud attempt: “Our customer said, ‘Hey, we think this is fake.’ We said, ‘You’re confirmed. Here’s the 17 things that were doctored on this invoice.'”

Simplified Pricing for Growing Teams

Unlike many software solutions that use per-seat pricing models, Routable offers unlimited users with pricing based on payment volume. The platform starts at $599 per month and scales based on throughput rather than user count.

“Typically, you give two to five people access to your bank, and you give maybe five or seven people access to your ERP, but your operations team might need access to ‘did this get paid?'” Omri explained. “There’s essentially an onion: finance, then fin-ops, then ops, then maybe customer success.”

This approach allows businesses to distribute access across departments without additional costs, fostering collaboration between finance and operational teams.

A Strategic Investment in Financial Operations

For finance leaders and accounting professionals, Routable is more than just a bill pay solution; it’s a strategic investment that transforms accounts payable from a transaction-processing burden into a business advantage.

Blake summarized, “The way you’ve built the sync to the ERP system or QuickBooks is so rock solid. Being able to pull everything in… it’s a dream as an accountant.”

When considering the return on investment, Omri offered a compelling perspective: “I’ve never met a CFO or director of accounting, or a head of a CPA firm who has enough budget. What if you could say, ‘Hey, if we catch fraud, we get that budget back?’”

Whether you’re managing finance for a growing business or advising clients navigating these challenges, exploring modern accounts payable solutions like Routable could transform what has traditionally been a back-office function into a strategic enabler for business growth.

To learn more about how Routable can help your business or clients transform their accounts payable processes, watch the full Earmark Expo webinar.

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

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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.