Technology Strategist Role Description

Posted Saturday, June 13, 2026

Thank you for your interest in WCG CPAs & Advisors. The following is high-level information for our Technology Strategist role, a new senior position created to connect the technology threads running through our firm and to keep WCG moving forward as the profession changes.

The next decade of tax and accounting will be shaped by firms that use technology well. WCG is already leaning in: the AI Tax Prep Pod launches in November 2026, the Biz Dev team is building transcript-to-proposal automation, and the rest of the firm is wrestling with how to integrate AI into research, planning, and client communication. What we do not have yet is a single person responsible for connecting those threads, sharpening what works, and helping us see what comes next.

That is what this role is.

Who Is WCG

WCG CPAs & Advisors isn't your typical CPA firm, and if you've spent any time in public accounting, you already know that's either a red flag or a relief. For the right person, it's the latter.

Headquartered in Colorado Springs with team members across the U.S. and in India, we're a methodically growing firm with 7 partners, over 90 full-time team members, and projected 2026 revenues of $12.7M, representing about 14% year-over-year growth. We grow because our model works, not because we say yes to everything.

We offer the depth of a mid-size firm with the focus and personality of a boutique. We play in specific sandboxes- small business owners in S Corps, Partnerships, and PCs; complex individual tax, and real estate investors, and we play in them very well. Real estate and rental activity planning alone represents over 40% of our advisory work and is our fastest-growing segment.

No billable hours. No six-minute increments. No stuffiness. We operate on a value-based, next-gen advisory model built around annual service offerings that combine tax return preparation, routine consultation, and strategic planning. A tax return, in our world, is the result of a year's worth of conversations, not a transaction.

If that sounds like the environment you've been looking for, keep reading.

Last updated- Sunday, April 19, 2026

WCG Team Overviews

Support Team

Everything starts and ends with our Support Team, and we mean that. Their mission is to make clients' lives better and to back up every other team at WCG. The Support Team runs in four lanes:

  • Client Support: Our frontline team handling phone calls, chats, texts, and general email inquiries. First impressions live here. The rest of the WCG team spends every day trying to live up to it.
  • Tax Support: Our largest segment and does the heavy lifting on both ends of the tax return process. They handle front-end data collection (IDP, which stands for Information and Data Processing... yeah, the name is a little stale, but the function is mission-critical) and back-end assembly using SurePrep. They also collect payments, obtain e-file authorizations via Canopy, and file about 75% of our tax return extensions.
  • Operations Support: Led by a full-time CPA and former tax manager whose job is to keep the trains running on time across all teams and to surface the right information to WCG leadership and Pod leaders.
  • Human Resources: Led by our dedicated HR Manager who ensures compliance, sure, but whose primary function is supporting the team with their needs from travel and IT to family leave, the firmwide calendar, and beyond.

Tax Prep Team

We use Thomson Reuters UltraTax in a dedicated hosted environment, paired with SurePrep (including 1040SCAN) for electronic binders and annotations.

For the 2025 tax year, our team will prepare approximately 5,800 returns, a clean 60/40 split between individual and business entity returns. Because our Tax team has a well-documented fondness for summers, we push hard to complete 65% of returns by April 15, leaving May through July open primarily for tax planning work.

Over 50 Tax team members make this happen, including our 11 dedicated team members in India.

Rental Expert and Tax Strategy Pod

Real estate and advanced tax planning are core niches at WCG, so we built a team specifically for them rather than leaving it to generalists.

The RETS Pod works behind the scenes to support our primary tax Pods on the technical heavy lifting: initial asset setups, cost segregation studies (including fun 3115/481(a) adjustments), the short-term rental loophole, and Real Estate Professional Status (REPS) analysis..

We use a structured three-session process (Foundation, Exploration, and Execution) to map a client's full tax exposure and build an actionable strategy. We replace promoter math with real math, stress-testing every advanced strategy against what we call the 3-Legged Stool: a client's actual cash, effort, and risk tolerance.

2025 tax returns due in 2026 was our first time with the RETS Pod (fka, the rental expert pod). We had some bumps and bruises, and we have a lot of growing yet to do. Our ideal world is for all rental activities and related niche investments be handled by the RETS Pod leaving the remaining pieces of the tax return to be completed by other WCG tax accountants. Two exceptions: a real estate holding company that files a partnership return, and a super simple 1040 where the rental and investment activities are the main event. Those get handled tip to tail by the RETS Pod.

If real estate tax strategy is your thing, this is where WCG is investing. We currently have 5 team members in this pod and are aiming for 9-10 by the end of 2026 to support our fastest-growing client segment as we continue the evolution from the original Rental Expert Pod to the 2.0, or the RETS Pod.

AI Tax Prep Pod (Coming November 2026)

WCG is actively building an AI Tax Prep Pod for the 2027 tax season, focused on AI-assisted preparation of individual (1040) returns. The thesis is straightforward: AI tools have evolved into something good enough and fast enough that a small dedicated team using them well can produce high quality and high throughput. The procedures, playbook, and standards do not exist anywhere yet. We are building them from scratch.

The Pod will operate similar to the RETS Pod: a specialized team with its own workflow, its own quality standards, and a direct line into the broader Tax Team. Tax returns prepared by the Pod will be reviewed by experienced reviewers using our standard quality controls. AI does not replace the review function. It changes the preparation function.

We are hiring the Pod Lead now. Podmates will be added as the role and the tooling mature. If you want to be part of building something genuinely new in this profession, this is the time.

Accounting Services Team

At WCG, Accounting Services means Bookkeeping + Analysis, not just reconciliations. There's a meaningful difference, and our clients feel it in their financial reporting, real-time tax planning, and day-to-day decision-making.

Our 11-person team (including a small group in India) each works with 25-30 clients using QuickBooks Online, Xero, and REIHub exclusively. No desktop, no Freshbooks, no whatever whatever. We also use Reach Reporting to give business owners a visual, trend-based view of their financials. Because a graph tells a story that a spreadsheet sometimes can't.

On cadence, we intentionally skip quarterly. Monthly, bi-monthly, and quad-monthly schedules let us smooth the workflow across the year so our team isn't buried in crazy Aprils, Julys, and Octobers. It's a small structural decision that makes a big difference for both the team and the client.

Accounting Services also handles sales and use tax filings and personal property tax. Clean, focused, genuinely valuable work.

Payroll Processing Team

WCG has processed payroll for over 800 small businesses for years. We're proud of that. But in summer 2026, we're making a deliberate shift, transitioning all payroll clients to ADP or Paychex for client-direct processing.

This isn't a retreat, it's a reset with intention. Payroll processing, done right, demands its own infrastructure, attention, and resources. By stepping back from it, we're doubling down on what we do best: high-level advisory, tax strategy, and the consultative work that actually moves the needle for our clients.

WCG is getting sharper on purpose. Read our Reset With Intention webpage for more information on our 2026 initiatives.

Business Development Team

Our 6-person Biz Dev team is the engine behind WCG's growth, specifically our advisory segment as opposed to tax-only engagements (we call those TOEs). They draft proposals, re-paper existing engagements, handle corporate governance matters like entity formations and S Corp elections, and own the onboarding process from first inquiry to fully engaged client.

The Biz Dev team works hand-in-hand with our Client Acquisition Team (the CAT) to make sure every prospect gets a thoughtful, human experience as they transition into a WCG engagement.

This isn't a sales team. Prospects come to us primarily through our website, content, and referrals. We average 6-7 inquiries per day, and 2 out of 3 are from high income earners who want tax reduction strategies through short-term rentals and other niche assets.

The Biz Dev team's job is to listen well, match the right engagement to the right client, and make WCG easy to say yes to.

Locations

In addition to over 35 remote team members, our physical footprint includes:

  • Headquarters: 2393 Flying Horse Club Drive, Colorado Springs, CO 80921
  • South Dakota: 300 North Main Street, Mitchell, SD 57301
  • Wyoming: 920 E Sheridan Street Suite B, Laramie, WY 82072
  • India: 705 Sankalp Square-3, Sindhu Bhavan Marg, Ahmedabad, Gujarat

Technology Strategist Intro

WCG has been technology-forward since 2007. We were online before online was a thing in our profession. But forward by 2007 standards is not the same as forward by 2026 standards, and the gap is widening fast. Tax research, return preparation and planning, and client communication, internal workflows, proposal generation, all of it is going to look different in three years than it does today. The firms that figure out how to evolve will look very different from the ones that did not. Dinosaurs? Might be dramatic, but not far off.

The Technology Strategist role exists to make sure WCG is not just a survivor but a thought leader.

You sit at the intersection of two priorities. First, you support the teams already pursuing technology and automation initiatives at WCG, helping refine workflows, evaluate tools, and connect what they learn back into the broader firm (current examples include the AI Tax Prep Pod and Biz Dev’s transcript-to-proposal automation). Second, and most importantly, you keep WCG on a forward tech trajectory by spotting opportunities, evaluating platforms, designing automations, and helping the firm decide where to lean in and where to wait.

This is not a traditional IT role, but it is not strictly above-the-fray either. We have a managed IT vendor for infrastructure, security, and end-user support, and you serve as WCG’s point of contact to that vendor. At the same time, you should be willing and able to get dirty when needed: troubleshooting a teammate’s workflow issue, helping someone get a new tool configured, or jumping in on a problem that does not warrant a vendor ticket. Your primary focus is the layer above IT, where technology meets workflow meets strategy, but day-to-day support work shows up too.

A few things worth saying directly:

  • This is a senior individual contributor role with leadership upside. You are not running a team yet, but you are influencing how multiple teams operate. As the function matures and the scope grows, the title and responsibility will grow with it. The expected trajectory is Technology Strategist to Director of Technology and Automation on a two to three year horizon.
  • The partnership path is real but not guaranteed. WCG promotes from within, and the technology function will become more central to the firm over time. Strong performance in this role is a credible path to Partner. We are not promising it. We are saying the trajectory exists.
  • You are building the function, not inheriting it. The Technology Strategist role does not exist at WCG today. You will define what it looks like, what it measures, and how it operates inside the firm. That is a feature, not a bug, if you are the right person for the role.
  • Accounting fluency matters. It is the preferred entry point, but not the only one. We hire either credentialed tax professionals with strong tech instincts or experienced technologists who can learn the profession. The right person can come from either direction. What matters is the ability to think across both worlds and connect them.

Is This You?

This role is a strong fit if you are…

  • A bridge builder. You can sit in a room with a tax professional discussing a client situation, then sit in a different room with a developer discussing an API, and translate fluently in both directions. This is the rarest skill on the list and the most important.
  • A pragmatic technologist. You evaluate tools by what they actually do, not what the marketing claims. You have opinions about ChatGPT versus Claude versus Gemini, about Zapier versus Make, about which problems automation solves and which it makes worse. You know what overengineering looks like and you avoid it.
  • Someone who can build light. Scripts, prompts, integrations, low-code workflows. You are not a software engineer and you do not need to be. But you can prototype something useful in a weekend without needing a team to do it for you.
  • Strategic and curious. You read about what other firms are doing, what other industries are doing, and what the AI labs are shipping. You think in three- and five-year terms, not just next-quarter terms.

A quick reality check…

This role lives in a CPA firm. The culture is collaborative, the pace is real, and the tax season rhythm shapes a lot of how decisions get made. If you are coming from a tech-only background, the cadence will be different from a startup or product company. You will need patience for the parts of accounting work that AI does not (yet) touch.

This is not a build-everything-yourself role. The center of gravity is strategic and oversight-driven. You will design, evaluate, recommend, and coordinate. You will prototype and ship light builds. You will not be writing production code or running a development team. If hands-on building or coding is the only thing that energizes you, this role will frustrate you. There is real hands-on work here, but it is service-oriented and pragmatic, not building-for-its-own-sake.

This is also not a role with a defined playbook. There is no template for what a Technology Strategist looks like at a boutique CPA firm in 2026, because there are not many of these jobs yet. You are figuring it out with us. If you need every process locked down before you can do your best work, the timing is wrong.

Small Warning

This role is new and will flex with the firm. From May through December, your focus is squarely on technology and automation. During tax season, especially in the first year or two, expect to roll up your sleeves on tax prep alongside the team. As the technology function matures, the role will shift toward full-time technology work, and some pieces may become seasonal as initiatives evolve.

This is part of why we lean toward candidates with a tax or accounting background. A credentialed tax professional with technology instincts can contribute on day one across the full WCG calendar. A pure technologist is an unlikely candidate until the role matures and WCG’s technology needs are more demanding year round. Once the technology function reaches that point, tech-side candidates become a more natural fit.

Basics

Applicants Must

  • Bring substantial experience evaluating, implementing, and integrating technology in a professional services environment. Three years or more of relevant experience is the floor. The specific path matters less than the pattern of results.
  • Have genuine AI fluency at the user level across multiple platforms (ChatGPT, Claude, Gemini, or specialty tools). Opinions, not just usage.
  • Be comfortable with light hands-on building: scripts, prompts, integrations, low-code automations. You should be able to prototype an idea without waiting for someone else.
  • Demonstrate strong written and verbal communication. You will be translating between technical concepts and business outcomes constantly.
  • Show evidence of strategic thinking. References, prior work, or examples that demonstrate you have shaped technology direction at a firm or team, not just executed someone else’s plan.
  • Be comfortable working across multiple teams simultaneously. The role spans Business Development, Tax, Accounting Services and Operations.
  • Have a Bachelor’s degree.

Nice To Haves

  • Prior experience inside a CPA, tax, or accounting firm. Cuts down ramp time meaningfully.
  • A CPA, EA, or CA credential. Not required, but signals you understand the work the firm does at a structural level.
  • Background in workflow automation tools (Zapier, Make, n8n) or low-code platforms.
  • Experience with tax-specific software (UltraTax, SurePrep, Canopy, or comparable platforms).
  • A track record of independent learning and shipping. Side projects, open-source contributions, prior automation builds at previous firms.

Compensation

$110,000 to $130,000 total compensation, depending on experience and the strength of the prior track record. The upper end of the range is reserved for candidates who can step in and contribute strategically from day one with minimal ramp.

Bonuses, based on contribution to firm initiatives and the maturation of the technology function. Bonuses, if offered, are considered in addition to total compensation.

Reporting Manager

Partner

Technology Strategist Role Responsibilities

You will work across multiple teams and report directly to a Partner. Your duties include WCG’s general firm responsibilities plus, or as modified by, the following:

Role-Specific Duties

  • Supporting teams pursuing technology and automation initiatives, including workflow design, tool selection, and process refinement (current examples include the AI Tax Prep Pod and Biz Dev’s transcript-to-proposal automation).
  • Identifying, evaluating, and recommending technology platforms for firmwide adoption (AI tools, workflow software, automation platforms, integration layers).
  • Owning software and technology reviews, including annual contract renewals, vendor evaluations, and platform consolidation decisions.
  • Serving as WCG’s point of contact to our managed IT vendor, coordinating support tickets, escalations, and contract matters.
  • Providing direct support to WCG teammates on workflow issues, tool configuration, and other technology questions that do not warrant a vendor ticket.
  • Designing and shipping light automations that solve specific firm problems, including scripts, prompts, integrations, and low-code workflows.
  • Serving as the internal subject matter expert on AI fluency and helping develop AI training for the broader team.
  • Acting as a strategic thought partner to firm leadership on technology direction, AI adoption, and the build-versus-buy decisions that come with both.
  • Tracking the broader technology landscape (AI labs, professional services tools, accounting industry developments) and translating relevant developments into WCG context.
  • Building the technology roadmap for WCG and refreshing it as the landscape changes.

General Firm Duties

  • Guiding WCG along the path of success.
  • Promoting WCG culture and encouraging excellence and high team morale.
  • Developing and implementing WCG goals, procedures, and policies in coordination with other Partners, Directors, Managers, and Associates.
  • Identifying improvement gaps and assisting with deploying corrective measures.
  • Providing feedback, concerns, and recommendations to WCG leadership.
  • Advancing WCG’s professional pursuits and brand presence in the technology and AI space, including with associations, peer firms, and industry forums.
  • Coordinating efforts across teams (Biz Dev, Tax, Accounting Services, Support).
  • Helping keep the workflow moving.
  • Other tasks related to firm operations, technology, and strategy.

Technology Strategist responsibilities and duties will change significantly as the role matures and as the technology landscape shifts. They are reviewed, modified if necessary, and agreed to during Associate Reviews.

Hours Requirements

All salaried positions must work 1,900 hours annually / 12-month trailing period. This is hands-on-keyboard, work-related time only. Holidays, office closures, PTO, and other paid time off do not count toward and are not deducted from the 1,900-hour requirement, because your time off is genuinely yours.

WCG does not set a weekly minimum number of hours. That said, for team members who follow the tax team work cadence, our experience historically is that 55-60 hours per week during tax season (roughly 10 weeks) and 50-55 hours per week during extension season (roughly 9 weeks) are needed to find success, with lighter hours the rest of the year (for example, 30-32 hours per week during summer). Other teams follow different cadences.

Please refer to the WCG Associate Handbook for additional information.

UPDATE! You might see reference to 2,100 hours elsewhere. As of June 8, 2026, we are moving to the 1,900 hour version above to simplify and remove confusion.

Technology Strategist Career Path

The Technology Strategist role is new at WCG, and the career trajectory is being defined alongside the role itself. The expected progression on a two to three year horizon is Technology Strategist to Director of Technology and Automation, with a credible path to Partner for the right person beyond that. WCG promotes from within, and the technology function will become more central to the firm over time.

The path is real. It is not guaranteed. The right person earns it.

For candidates who prefer to stay in a senior individual contributor role without pursuing Director or Partner, that path is also available. WCG does not force people into leadership tracks that do not fit them.

How To Join The WCG Team

Here is the step by step process-

  1. Click on the button below to complete a quick Candidate Questionnaire and upload your resume.
  2. If we like your detailed and thoughtful responses, we schedule a Teams chat with Jason Watson. It is slated for 75 minutes to give you plenty of time to get your questions answered and gain familiarity, though it often runs shorter. This is purely to get a feel for each other. We can teach you anything… short of being nice, being professional, being energetic, being someone we can work with. Taxes? Easy. Accounting? Got you. Ability to hold a meaningful conversation? Well…
  3. After that initial meeting, and if we believe there is a basis to work together, we ask you to complete our Fit Alignment Assessment. It takes about 30 minutes and helps us understand where you would slot in. Most WCGers have taken it, so we have a good baseline. We are cautious with how we read it- it is not pass or fail, and it usually just underscores what we already gleaned from your questionnaire and our chat.
  4. Next, we introduce you to our recruitment team of Megan, Terra and Beth. After you chat with at least two of them, we get together and talk behind your back.
  5. Finally, Jason checks in to see if you have any additional questions, and to start formulating a role with the team, compensation, start dates, etc. Then an offer letter is presented. Yay!
  6. Once an offer is accepted, then there might be a lot of radio silence depending on start date. As things get closer, we order a background check. For remote positions, we also do a tech survey to see what you need, and we start to discuss travel plans.
  7. About 30 days before your start date, training materials and a schedule are presented.

And away we go!

join the WCG team

Join The WCG Team

Apply online to join the team- answer some questions and upload a resume!

Apply Online!

WCG Careers

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2026 Benefits

WCG 2026 benefits summary outlines health insurance (United Healthcare Choice Plus HDHP, employee-only), dental, and vision coverage.

Associate Handbook

This Associate Handbook was developed to describe some of the expectations we have for all associates and what you can expect from WCG.

WCG CPAs & Advisors is a full service consultation and tax preparation firm located in Colorado Springs, Colorado, and we look forward to working with you!

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