The most successful digital asset tax reporting projects don't start with vendor evaluations—they start with internal alignment.
Many financial institutions preparing for Form 1099-DA begin in the same place: drafting an RFP.
On paper, it seems like the logical first step. Identify requirements, send them to potential vendors, compare responses, and select the best solution.
But organizations that approach digital asset tax reporting this way often discover a problem months later: they never aligned internally on what they were actually trying to solve.
The reality is that a Request for Proposal is only as good as the operating model behind it. If the institution hasn't identified the right stakeholders, defined its reporting obligations, or agreed on what success looks like, even the strongest software provider will struggle to deliver a successful implementation.
As discussed during Ledgible's webinar, Building a 1099 Operating Model for Success, organizations should think of an RFP as the outcome of planning—not the beginning of it.
Start With Business Objectives, Not Software Requirements
One of the first sections of any RFP should establish its purpose, summarize the project's objectives, and provide background on the organization. While this may seem like administrative work, it serves a much more important function.
Suppliers need context.
Without understanding an institution's products, customer base, organizational structure, and reporting obligations, vendors are left making assumptions about implementation scope, pricing, and required functionality.
As Wendy Walker, VP of Regulatory Affairs at Sovos, explained during the webinar, these opening sections provide suppliers with the background they need to deliver meaningful responses rather than generic proposals.
For institutions, that means clearly defining:
- Why the project exists
- Which regulatory requirements it addresses
- What products and business lines are involved
- What outcomes define success
An RFP should communicate far more than a list of software features—it should tell the story of the operational challenge the institution is trying to solve.
Tax Reporting Isn't Owned by One Department
One of the biggest mistakes organizations make is assuming Form 1099-DA is solely a tax or compliance initiative.
In reality, digital asset reporting touches nearly every major function within the organization.
The tax team may interpret reporting requirements.
Compliance manages regulatory risk.
Engineering owns transaction data.
Product teams define customer workflows.
Legal reviews obligations.
Customer service fields questions from customers receiving tax forms.
Operations manages filing and reconciliation.
Each group brings a different perspective—and different priorities—to the procurement process.
The webinar highlighted that successful RFPs identify not only the primary decision makers, but also the stakeholders whose day-to-day responsibilities will ultimately determine whether implementation succeeds.
The Stakeholder You Probably Forgot
One of the most insightful moments during the discussion centered on customer service.
Jessalyn Dean, Senior Policy Advisor for U.S. Tax Reporting at Ledgible, noted that organizations frequently build vendor evaluations around regulatory compliance while overlooking the teams responsible for supporting customers after tax forms are delivered.
That imbalance can have significant consequences.
A solution that satisfies every regulatory requirement but creates unnecessary customer friction may not be the best solution for the business.
Customer service teams often understand pain points that aren't visible during procurement:
- Questions customers ask most frequently
- Common onboarding challenges
- Documentation issues
- Communication preferences
- Support workload during tax season
Bringing these teams into the conversation early often changes how organizations prioritize vendor capabilities.
Define What Is Actually in Scope
Before evaluating vendors, institutions should conduct a thorough product analysis.
Digital asset businesses rarely operate a single product.
A single institution may offer:
- Retail trading
- Institutional custody
- OTC services
- Staking
- NFT marketplaces
- Tokenized securities
- Traditional investment products
Not every product carries the same tax reporting obligations.
Not every product requires cost basis calculations.
Not every product requires withholding.
The webinar emphasizes that understanding which products are—and are not—in scope is one of the most important planning exercises before drafting an RFP. It ensures vendors understand exactly what they're being asked to support and prevents costly implementation surprises later.
Alignment Improves Vendor Responses
One of the hidden benefits of building an operating model first is that vendors can provide more accurate proposals.
When institutions clearly communicate:
- Transaction volumes
- Customer populations
- Product lines
- Implementation goals
- Existing systems
- Success metrics
Suppliers spend less time making assumptions and more time proposing practical solutions.
That leads to:
- Better pricing
- More realistic implementation timelines
- More accurate scope estimates
- Better demonstrations
- More meaningful comparisons across vendors
An RFP should make it easy for providers to understand the business—not force them to guess.
Success Requires More Than Software
Another recurring theme throughout the webinar was that institutions shouldn't expect software providers to solve organizational challenges.
Technology enables compliance.
It doesn't replace governance.
Successful implementations require internal decisions around:
- Ownership
- Data governance
- Customer communications
- Operational workflows
- Escalation paths
- Regulatory interpretation
The stronger these decisions are before vendor selection, the smoother implementation becomes.
Conversely, organizations that postpone these conversations often find themselves revisiting major decisions after contracts have already been signed.
Build the Operating Model First
The temptation to move quickly into software evaluations is understandable. Regulatory deadlines create urgency, and organizations naturally want to begin evaluating providers as soon as possible.
But the strongest digital asset tax reporting projects begin with a different question:
How should our organization operate?
Once that answer is clear, the right software becomes much easier to identify.
An RFP isn't simply a purchasing document—it's a blueprint for how an institution intends to manage digital asset tax reporting for years to come.
Investing time upfront to align stakeholders, define scope, and establish business objectives pays dividends throughout implementation and beyond.
Watch the Full Webinar
Building a successful 1099-DA operating model requires more than selecting software. It requires aligning people, processes, and technology around a common compliance strategy.
In the on-demand webinar, experts from Ledgible, Sovos, and Comply Exchange walk through the complete RFP framework, discuss stakeholder alignment, and share practical guidance for preparing your organization before vendor selection.
Watch the on-demand webinar: https://ledgible.io/on-demand-webinar-building-a-1099-operating-model-for-success
Whether you're drafting your first digital asset reporting RFP or refining an existing procurement strategy, starting with the right operating model can make the difference between a smooth implementation and an expensive course correction.
