QUICKBOOKS CONTRACTOR ECOSYSTEM

BUILDING A TRUSTED PLATFORM FOR SELF-EMPLOYED CONTRACTORS AND SMALL BUSINESSES TO WORK WITH EACH OTHER THROUGHOUT THE YEAR.

In 2016, after QuickBooks Self-Employed continued to grow rapidly, the Intuit Small Business Group (SBG), which managed the QuickBooks line of products, finally recognized Self-Employed Contractors as an essential customer base alongside Small Businesses and Accountants by updating the business unit’s name to be Small Business and Self-Employed Group (SBSEG)—which was a huge accomplishment for those of us who had focused on the serving the needs of Self-Employed Contractors and had fought hard to establish Self-Employed Contractors as an important group of customers for the prior year.

During this change, a growing number of team members and executive leadership observed that many QuickBooks Self-Employed customers appeared to work Small Business clients themselves. Similarly, numerous observations of how frequently QuickBooks Online Small Business customers worked with Self-Employed Contractors were also made. Naturally, this led to a series of questions and discussions throughout SBSEG about how often this happened, the challenges these customer bases may be experiencing while working with each other, and whether there was an opportunity for QuickBooks to serve them better.

Since the extensive research I had driven in the past helped inform the core features developed for QuickBooks Self-Employed, I was chosen to lead a six-week Discovery phase to investigate the answer to those questions in partnership with a Project Management Intern. Our initial investigation uncovered critical insights about the challenges that many Self-Employed Contractors and Small Businesses faced when working with each other, how our products were contributing to those problems, along with a massive opportunity that QuickBooks was uniquely poised to solve for two of its three primary customers.

Thrilled by our insights, our executive sponsor asked my partner and I about what a “gold standard” experience would look like. To answer this, we both spent the following three days transforming our insights and opportunities into a story-based vision which we vetted with customers before sharing back with our team and leadership. That vision illustrated a better world where QuickBooks could become a trusted platform for Self-Employed Contractors and Small Businesses to work with other throughout the year—and even evolve to a “Find jobs/contractors” platform.

After viewing the vision of how our previously disconnected QuickBooks products could bridge together to support these two core customer bases, leadership and product teams’ excitement was sparked, passionate conversations flowed across SBSEG, and eventually enabled us to receive the leadership support and resources to grow a mission team so we could bring this vision to life. Starting with Discovery Phase, to Experiment Phase, and leading to the launch of the Minimum Lovable Product, this case study details my journey to provide better ways for Small Businesses and Self-Employed Contractors to work with each other.

The views reflected in this case study are my own, and not those held by Intuit or QuickBooks.

OUR EARLY DISCOVERIES

SETTING UP THE INITIAL DISCOVERY RESEARCH

To ensure that we would maximize our limited six-week timeline allotted for Discovery Research, my partner and I decided to divide and conquer. After listing and prioritizing the questions to answer, identifying participant groups we wanted to research, along with a list of our hypothesis about them—we planned, coordinated, and delegated our research efforts based on our personal strengths. My partner drove the quantitative data insights and I drove the planning, screening, recruiting, coordination, facilitation, and synthesis of qualitative research sessions.

We recruited and spoke with a diverse group of 26 research participants, including:

11 Self-Employed Contractors
11 Small Businesses
2 Accountants
2 Hybrids
(they worked as contractors themselves at times, but also owned a small business that hired other contractors)

To avoid biasing our research to the current QuickBooks experience, we included both existing QuickBooks customers as well as non-customers. After synthesizing our six-week Discovery Phase, here’s what we learned…

OUR QUALITATIVE FINDINGS FED US HUMBLE PIE

BIG TAKEAWAY: Pain points are not one-sided or limited to single moment.

The single, biggest takeaway from our initial discovery research was how interconnected these two types of customers were once they decided to work with each other. If one encountered a challenge that went unresolved, chances were high that it would impact both sides long after their work was completed. This would help our team understand the pitfalls of designing within artificial business-based silos that prevent us from solving for our collective customers in an inclusive, holistic, and and systematic way.

Aside from the big takeway above, below are the three key supporting insights which you can expand for additional details:

+ KEY INSIGHT 1: Oversights in onboarding can avalanche into distressful cashflow uncertainty about what's owed and when.

At the start of their working relationship, most Self-Employed Contractors and Small Businesses have a tendency to skip ahead to what they know and are passionate about: Their work.

After an initial agreement about the compensation amount, many don't utilize contracts to document those agreements about the work scope, how they'll work together, and steps to take if anything unexpected happens. A surprising majority don't require W-9 forms to be signed, leading to tax time risks and penalties. Many Small Businesses and Self-Employed Contractors proceed to work together without discussing the process of getting paid, which includes how to invoice, what to include in the invoice, when to invoice, net terms, and payment methods.

Without discussing these expectations or documenting their agreements earlier, these seemingly minute oversights can quickly avalanche into more significant cashflow problems. For instance, a Self-Employed Contractor without guidance may continue working for a few months before realizing that they must invoice to get paid. By this point, the contractor likely needs the money urgently. As the contractor prepares their invoice by relying solely on their memory, they risk neglecting to include services or hours that would remain forever uncompensated. Even after sending the invoice to their Small Business client, there's uncertainty whether the invoice has been viewed, approved, and when the payment comes—which causes emotional turmoil because they hesitate to badger their clients for fear of ruining their work relationship.

Consequently, although their Small Business client may have agreed to a certain estimated amount or hourly rate, they often don't know when that invoice will come, how big it can get, how quickly they'll have to pay it. Needless to say, the consequences of a large, abrupt bill like that can have a damaging impact on their cashflow. Over time, these issues continue to multiply and often come to a head at tax time when both parties scramble to gather data for their "source of truth," estimate their tax bill, and ways to reduce it.

+ KEY INSIGHT 2: In the current system, doing everything right doesn't eliminate cashflow gaps and unexpected tradeoffs.

Like QuickBooks, most products like to believe that if our customers leverage their services to do everything right, they'll be guaranteed better outcomes. However, we quickly learned that this was not the case with how the current QuickBooks system was designed.

Despite doing everything right and leveraging every possible QuickBooks feature at the time, customers would still encounter cashflow gaps. This could come in the form of delayed payments that forced them to leverage other "layers of money," such as savings, loans, or credit cards to cover those gaps. It could also mean investing a considerable amount of time to make those funds available within their bank account.

For instance, even a seasoned Self-Employed Contractor who submits their invoices on time and to multiple contacts within the Small Business organization may get paid 6 months after sending a net-30 day invoice—and that's despite regularly following up with the appropriate contacts. In other instances, Small Businesses intentionally chose to pay Self-Employed Contractors with paper checks because it enabled them to float that money to cover additional operational costs. Small Businesses could deliberately delay the payment by choosing to mail a check, which bought them 3-7 days of waiting until their next in-person meeting to hand the paycheck to the contractor, which depended on scheduling a time when both were available to meet. Once they had a paper check in hand, the next issue the Self-Employed Contractor had to worry about was how to deposit those funds into their bank account. Suppose the contractor has a mobile bank app that excludes large mobile deposits. In that case, they'd need to plan a trip to the bank during their workweek to stand in line and deposit the check—which could translate into significant opportunity costs for them.

+ KEY INSIGHT 3: The high stakes during tax time make it one of the most confusing, scary, and frustrating tasks for both.

The good news here was that everyone wants to do the right thing.

The bad news was that many just don't know how, and we as QuickBooks were not making it any easier for them.

Due to the lack of guidance and guardrails within QuickBooks, there was a proliferation of misinformation that often leaves both parties to seek a source of truth, chase after missing data, and explore other solutions to avoid the eleventh hour tax time scramble.

During tax time, many Small Businesses realize for the first time that they need to prepare and send their Self-Employed Contractor a 1099-MISC tax form and that they need a completed W-9 form to do this. Yet, when they request this info from their contract, they can experience challenges in retrieving it because the contractor's contact info may have changed, or they don't feel inclined to complete a W-9 form for work that was concluded and paid for months ago. This can ultimately jeopardize the Small Businesses' ability to claim those contractor payments as a deduction or, worse, be penalized with fees. Similarly, a Self-Employed Contractor who hasn't received their 1099-MISCs on time can experience uncertainty and frustration about how to proceed, especially if a Small Business is unaware of their obligations to send their contractors a 1099-MISC tax form. Again, this can ultimately lead to potential tax compliance risks and penalties for both.

Lastly, if the total amounts appear to be different for either party, it can lead to audits from the IRS, and yet again—compliance risk and penalties for both parties. For the reasons listed above, it's strongly advised by seasoned Small Businesses, accountants, and tax experts to have the Self-Employed Contractor complete a W-9 form when they initially began working together regardless of the actual amount they would get paid.

Apart from the key learnings above, we also came across a few other interesting points:

Three of the four Small Businesses participants we spoke with had not added their contractors to QuickBooks because they’d already adopted other platforms to onboard, pay, and file tax forms to continue working with their contractors.

Due to QuickBooks’ lack of contractor-oriented features and inconsistent language, many Small Businesses adopted other platforms and apps that made it easier to work with Self-Employed Contractors which is why they never entered them into QuickBooks. Interestingly enough, every Small Business mentioned strongly considering switching to QuickBooks if and when it made it easier to work with contractors because apart from centralizing their accounting information, they could leverage deeper insights, they would prefer to use a brand that has established a long legacy of trust when it came to sensitive information.

**Self-Employed Contractors and Small Businesses actually preferred to work with each other on a regular basis.**

Another surprise was learning about how much these two customer bases actually preferred working with each other and how carefully they went about it to ensure that it didn’t conflict with government regulations.

Many contractors explained how working with small businesses gave them greater flexibility to payments and net terms compared to working with a larger organization with more rigid structures, longer payment periods, and being passed between departments to resolve any issues. Also, if anything went sideways, they would also have a clear contact they could reach out to for a swift resolution to the issue.

For Small Businesses, having a group of contractors was like having a flexible, trusted S.W.A.T. team they could enlist anytime the need arose and who would develop a deep understanding how to best adapt to their business needs over time. Working with contractors was also very appealing for newer Small Businesses who didn’t feel like they were profitable or steady enough to hire employees.

OUR PRODUCTS WERE CAUSING MORE PROBLEMS THAN THEY WERE SOLVING

Hearing about customers’ challenges with using QuickBooks, my partner and I decided to do a deeper product audit which revealed many issues…

At this point in time, the only way for a Small Business could manage Self-Employed Contractors using QuickBooks was by subscribing to its then highest tier: QuickBooks Online Plus. QBO Plus could track “1099 payments” which usually had to be manually entered into the system and it did not include actually being able to pay their contractors. To pay contractors via QuickBooks, Small Business customers needed to add Payroll for an additional cost which would enable them to pay contractors only by paper check.

To make matters worse, although we had “manage 1099 contractors” on our price comparison chart, there was no mention of “contractors” anywhere within QBO Plus. Instead, like other QBO products, Self-Employed Contractors were lumped as “vendors” without any explanation to our customers. This caused bigger problems for Small Business customers because unlike Self-Employed Contractors, vendors usually didn’t need to be issued a 1099-MISC because they were usually small businesses themselves, and nor did this map to how Small Businesses thought about their Self-Employed Contractors. Additionally, if a Small Business somehow forgot to check that “track as 1099” checkbox when adding a contractor as a vendor, they couldn’t fix it. They’d have to go back to re-add the contractor again and continue to have a wrong duplicate in their vendor list which could cause other problems. These mistakes happened frequently because a Small Business customer would get overwhelmed by all the fields to complete in the Vendor form. Most customers would simply add a name, ignore the rest, and likely realize the consequences of their mistake months later when they realized at the eleventh hour of tax time that they needed to send a 1099.

Our early customer sessions also helped us realize that many Small Business customers who were subscribed to the other tiers QuickBooks Online were actually more likely to work with contractors than employees because it better fit their business needs. Yet, virtually every QuickBooks Online product made no mention, provided zero guidance, or ability to track 1099 payments (which was reduced to a tiny checkbox available only in QBO Plus).

A few weeks later, we learned from the QuickBooks Online Payroll team that paying contractors electronically amongst the top five requested features over the past few years.

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OUR QUANTITATIVE FINDINGS REVEALED A HUGE, UNTAPPED OPPORTUNITY

Despite these challenges in using QuickBooks for working with contractors my partner’s conservative calculations taught us that:

QuickBooks Online Plus Small Business customers alone had paid a total of 3 million contractors in 2016.

When we took into account all of the Small Businesses and Self-Employed Contractors who use other tiers of QuickBooks Online and work with contractors whom may or may not be paid using QuickBooks, we were looking at an untapped customer base of at least 17 million Self-Employed Contractors working with 24 million QuickBooks Online Small Businesses customers.

Furthermore, we learned that only 2% of those contractors used QuickBooks products, and only 10% of them used TurboTax products. If we were to expand our data parameters to include the other Small Businesses and Self-Employed Contractors who work with contractors but use other QuickBooks tiers, our initial conservative estimate of 3 million potential Self-Employed Contractors being paid by 1.5 million QuickBooks Online Small Businesses could actually double or even triple in size.

Business-wise, this presented a massive acquisition opportunity for QuickBooks and for our sister business unit, TurboTax, to support our collective customers in a way that we were already well equipped for.

LIGHT AT THE END OF THE TUNNEL

Overall, these learnings helped SBSEG understand how our past approach, which was territorial and siloed at times, actually did a big disservice to our collective customers because it increased effort for both sets of customers, made it easier to make unnecessary mistakes that unknowingly exposed both them to risk, and required more time and money to fix than either had bargained for. It also pushed Self-Employed Contractors and Small Businesses to look for partial solutions outside of the Intuit—which was a losing scenario for all of us because despite. To make it worse, despite paying more time and money to hack together a system outside of Quickbooks, our customers were still not guaranteed a better outcome.

This was something we could no longer afford to do, especially given a study released by Freelancer’s Union and Upwork about the nearly 54 million self-employed within the United States alone and how that number was expected to grow even higher.

The big light that we saw at the of the tunnel, was realizing how we as QuickBooks could come together to connect our platforms, fix these mistakes, and that we were uniquely poised like no other organization to do it in a way that encourages trust, protects sensitive data, and even go far as automating parts of this to promote prosperity our customers.

THE MINIMUM LOVABLE PRODUCT (MLP) WE BUILT TO SOLVE THIS

With support and resources from leadership, our team of two grew into an official Contractor Ecosystem Mission Team of 30+ individuals—and then gradually grew to 50+ individuals within a year. During our first few months, our team developed and launched a few in-product experiments for Onboarding and Tax Time. These initial two launches, v0.5 and v1, our team had to scale back the customer experience to optimize for speed and cost, but also so that our developer partners could focus on building the architecture and bridges necessary for this data flow to happen. The changes our ecosystem vision proposed would require us to make bigger changes throughout multiple QuickBooks products which is why these initial experiments helped us gradually learn, de-risk, and quantifiably prove that we were on the right track. This learnings and success from these initial experiences also helped our mission team to receive continued support to evolve the ecosystem experience.

Within a year of forming the Contractor Ecosystem mission team, we launched our v2—which we fondly referred to as the Minimum Lovable Product (MLP). We considered this to be the first version which contained the essential features necessary to provide a better-quality, lovable experience for our Small Businesses and Self-Employed Contractors.

As the primary designer who co-founded the Contractor Ecosystem Mission, conceived the vision, and gradually launched it piece by piece over the course of two years, I continued to enhance the interactions, visuals, and content, build interactive prototypes, and deliver specced-out assets to our product development partners. By the time we wanted to made updates to the MLP, many of our borrowed design resources were pulled into urgent projects by their original product teams which left me and a part-time visual designer to go continue updating the experience.

Below, you can watch videos about the Contractor Ecosystem end-to-end MLP experience, learn more about the process used to get there, and its outcomes.

ONBOARDING

INVOICING & PAYMENTS

TAX TIME

THE OUTCOME

WE WERE OFF TO A GOOD START

Here’s a summary of what we accomplished in under two years (you can expand each for more details):

+ We bridged together five disparate Intuit products to simplify lives for Self-Employed Contractors and Small Business customers.

If a Small Business and Self-Employed contractor worked together using QuickBooks, Small Business customers would no longer have to worry about making mistakes as frequently as before, having to re-enter data manually, nor worry about data accuracy. They also didn't have the same tax time scramble because the information was populated automatically and double-checked with the contractor's data for discrepancies.

+ We made managing contractors accessible across all QuickBooks Online products—except QuickBooks Self-Employed (which I hope will include this feature someday)

No longer did Small Businesses have to worry about upgrading to the highest tiers of QuickBooks Online to track the payments they made to Contractors. They also no longer have to pay for the full QuickBooks Payroll service to pay a single contractor. We were able to update the former "Employees" tab as become "Workers" tab (which was a deviation from our preferred "Workforce" tab) that includes both Employees and Contractors. The "Workers" tab is now called the "Payroll" tab as part of the recent updates.

+ We made the language consistent across our products to reduce errors and confusion.

68,000 QuickBooks Small Businesses invited their contractors to self-set-up—which led to 78,000 Self-Employed Contractors who completed their self-set up info. This feature didn't exist before.
We piloted the Contractor Payments MLP with only 5,400 QuickBooks Small Businesses. They wound up paying over $48 million dollars to their contractors via direct deposit within the first 6 months. One business paid up to 22 contractors, and the average contractor payment was $2,875. This feature didn't exist before.
We saw 1 million QuickBooks Small Businesses e-file 1099s, which was a 91% increase from the original experience. Approximately half of them opt to e-deliver 1099s to their contractors, which was a feature that didn't exist before.

+ Based on the data from 2018, within the first 9 months of gradually launching our Minimally Lovable Product, we had over 500,000 active customers within the ecosystem, generated over $1 million dollars in revenue. We reached these numbers with little to no marketing effort.

By distinguishing between "Vendors" and "Contractors" more consistently across QuickBooks Online products, we helped our customers avoid confusion and oversights. We've also introduced checkpoints in the right places. For instance, if a Small Business customer attempts to pay a contractor with an incomplete W-9 tax form, they're notified about the risk of paying without collecting the W-9 form first (and be one click away from sending a simple link to the contractor to self-set-up this info).

+ Because of its success, the interaction patterns and features introduced by this ecosystem were scaled to solve other problems and enable Employees to self-set up, too.

Shortly after releasing Contractor Self-Set up, the QuickBooks Online Payroll team leveraged the pattern to allow employees to self-set up their W-4 form details as well. It may also soon be scaled out to help Vendors complete their information as well.

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WHO WAS INVOLVED

MY ROLE AND RESPONSIBILITIES

As the earliest founding member of the opportunity and co-mission lead of a 50+ member team (primarily built with borrowed resources from other product teams), I leveraged my end-to-end product innovation expertise to serve as both a design leader from the bird’s eye view and a ground-zero, hands-on designer who generated detailed pixel-perfect designs.

During my involvement on this project over the course of two years, my responsibilities included serving in the following roles (expand each for more details):

+ Lead Design Researcher

Leading qualitative discovery research, synthesizing research into key actionable insights and opportunities, and conducting numerous co-creation exercises and usability studies to continue refining the experience. I also coached team members (designers and non designers alike), developed resources, and defined best practices that streamlined our research standards without compromising on integrity.

During my time on this project, which was just under 2 years, I drove a total of 94 customer sessions.

+ Innovation Strategist

Leading efforts to develop a shared strategy with stakeholders, facilitating creative collaboration, identifying leap of faith assumptions (LOFAs), developing experiments and a learning plan to test the riskier parts of the experience, defining and monitoring success metrics, prioritizing feature sets, keeping a feature backlog, and creating contingency plans for various outcomes in advance.

+ Design Leader and Mentor

Regularly sharing progress with executive leadership, developing a customer-vetted vision for target state, aligning stakeholders, influencing partner teams and coordinating roadmaps, allotting budgets and resources, growing the team, defining project scopes, developing op-mechs and frameworks to streamline our workflow. To help nurture our team, I also began to facilitate regular Design Workjams/Reviews, prepare resources to accelerate the design team, coordinate monthly Ecosystem Team lunches in collaboration with the Ecosystem Leader, and working with the other Mission Team leads to prepare email updates for the broader org where we shared our progress, milestones, metrics, and celebrated team members.

I led and directed eight designers across four different workstreams along with other cross-functional team members. I also managed two contract design team members.

+ Designer (User Experience, Interaction, Visual, and Content)

Designing comprehensive flows for the initial vision, outlining the customer journey map, prioritized features and narrowed the scope for MLP, created detailed wireframes for the end-to-end experience which included interaction and visual patterns, organizing the information architecture, and adapting existing design system patterns elevate a multi-stakeholder customer experience. I had to frequently switch altitudes between the birds-eye view and all the way down to the ground zero granular details to ensure that the experience remained consistent for both customers while being able to support our business needs as well. As designs were finalized for each stage, I delivered pixel-perfect assets to our build partners via Zeplin, and in the absence of content design resources, I occasionally wrote customer-vetted content to optimize and standardize how benefits were communicated across the ecosystem.

+ Prototyper

Building rapid prototypes using Invision, Adobe XD, and Figma to visualize interactions, test concepts, get feedback from customers and stakeholders, refine the product experience, and communicate behavior to build partners.

THE MISSION TEAM

There were many fluctuations in the team size during my time on this project. We started this project with two (including myself) and wound up growing to an official Contractor Ecosystem Mission Team of 50+ individuals.

The Discovery Phase included my Project Management Intern partner and myself. At the conclusion of the Discovery Phase, my partner went back to school to finish her degree.

During the Preparation Phase, leadership and the other product teams had a few additional questions that they wanted us to investigate and prepare before investing additional resources towards building the Contractor Ecosystem. For this phase, we grew to a core team of three (expand for additional details):

+ A new Product Manager/Lead

The Product Manager assisted with a few business model aspects, but primarily dove deeper to investigate the technical and product implications. The Product Manager also estimated the type of engineering resources we would need based on our technical challenges.

+ A new Marketing Manager/Lead

The Marketing Manager focused on the quantitative data, financials, and business aspects of the what we’d require, as well as where we could pull in funding from. They worked with data scientists to verify the data and build projections.

+ Myself as the Design Manager/Lead

I assisted these efforts to provide feedback on business considerations from a customer experience point-of-view, the design resources that out team would need as well as estimations on how they would need to be distributed and for how long. The Project Manager and I also investigated existing work we could leverage as well as key partners we could collaborate with. The three of us collectively worked on developing an early roadmap, the milestones, and scope. 

Once these preliminary estimations were completed, we presented options to leadership about how we could bring the Contractor Ecosystem to life so they could approve, support, and provide us with resources. Below were the options we’d identified on how Intuit could start building the Contractor Ecosystem, which you can expand these for more details.

Markdown Block:

+ Option 1: Keep Mission team small, tight, and nimble

What this looked like: We'd proceed with small, core team of 3-4 Mission Team Leads, and potentially bring in 4 additional existing employees to be fully dedicated to the ecosystem for the duration required.

The Rewards: This would enable the mission to move forward without dependencies, deliver a higher-quality product, and collaborate with other teams as need.

The Risks: The Time to delivery could be slower even though we could deliver a higher quality product. We’d need time to identify and pull others in, could potentially have misalignments with other product teams if not carefully coordinated, and our pace to deliver might take more time due to our limited resourcing.

+ Option 2: Borrow resources to expand Mission Team

What this looked like: Proceed with a small, core team of 3-5 Mission Team Leads who can identify and collaborate with key partners by adjusting their roadmaps and temporarily borrow their teams’ resources (e.g. Project Manager, Designers, Engineers).

The Rewards: This would be the fastest way to move forward and the borrowed resources could become liaisons who bring domain expertise as well as had prior knowledge of Intuit. They could also share back updates and become change advocates within their own corresponding product teams.

The Risks: This option had the heaviest form of dependencies on other teams which could mean fluctuations in project resourcing and pace. It might not be the best solution for the longer term.

+ Option 3: Open headcount to recruit for Mission Team

What this looked like: Proceed with a small, core team of 3-4 Mission Team Leads and recruit 6 additional dedicated individuals to drive this mission forward without dependencies.

The Rewards: This approach could provide us with maximum stability in the longer term when compared to other options.

The Risks: Going through the process of approving headcount, undergoing recuiting efforts, and onboarding new employees would likely take the longest period of time.

Our leadership decided move forward with Option #2 for the sake of speed and cost. This enabled the three of us Ecosystem Leads—The Marketing Manager, the Product Manager, and myself—to identify, align, and collaborate with specific products teams, including the broader Quickbooks Self-Employed team (where all three of us team leads were from), the QuickBooks Online Payroll team, and the Intuit Online Payroll team.

During the Implementation Phase, our team began to grow steadily until it reached 50+ individuals which included 3 Project Managers, 8 additional Designers (Interaction, Content, and Visual), Engineers (Front-end, Back-end, and Architects), Data Scientists, and a Legal counterpart. We needed to distribute our Mission Team to cover and simultaneously build out 6 separate workstreams—Onboarding, Invoicing and Payments, and lastly, Tax Time. Each of these would have a corresponding experience for Small Business and Self-Employed Contractor customers. For additional details about the workstreams, you can expand the lists below:

To help set the Contractor Ecosystem Mission Team up for success, executive leader also made a strategic decision to recruit a Contractor Ecosystem Leader who could help direct the three of us Mission Leads (Marketing, Product, and Design), and who would serve as the primary point of contact for executive leadership.

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MORE DETAILS ABOUT HOW WE GOT THERE

Based on our learnings, it became apparent how critical the onboarding process was to ensure a smooth year-round engagement with better outcomes for Small Businesses and Self Employed.

OUR NORTH STAR, PRINCIPLES, AND INSPIRATION

To help our team stay focused and on-track to deliver the solutions that mattered most, we defined our mission as a north start to guide us. Additionally, we gathered a wide range of inspiration from other services and helped us form principles for our overall experience.

From our large pool of inspiration, the three services our research participants frequently referenced for offering the best kind of experience were HoneyBook, Venmo, and Bonsai.

EARLY BRAINSTORMS

OUR INITIAL VISION

Within three days of our executive sponsor’s request to visualize what a “gold standard” experience would look like, here’s the customer-vetted vision that I put together based on some of the insights, opportunities, ideas, and feedback we’d gathered from Self-Employed Contractors and Small Businesses who worked with each other.

CREATING A BUSINESS STRATEGY TO STAND OUT IN A COMPETITIVE MARKETPLACE

Going into this, our team already knew that the QuickBooks Contractor Ecosystem had competitors who were already focused on supporting Small Businesses that worked with Self-Employed Contractors.

Based on our conversations with customers and our investigations, we realized that there still wasn’t a single all-in-one solution that met our customers needs within one platform. Many competitors were offering fragmented services that customers would have to manually hack together to create their own ecosystem—which was expensive, complicated, and buggy. This meant that our best shot would be to deliver a dual-sided, holistic, centralized, cost-effective features that could streamline our customers’ efforts throughout the year without getting in their way. Our biggest advantage was the fact that we already had QuickBooks Online products that served Small Businesses, as well as one that served QuickBooks Self-Employed Contractors—along with other relevant accounting and payroll products that simply needed to be expanded or tweaked.

To develop our business strategy, the Mission Team Leads (Ecosystem Leader, Marketing Leader, Project Management Leader, and myself as the Design Leader) collaborated on investigating the competitive landscape, demonstrating how we could position our offering in the market as the strongest option, and explore various pricing models for the business (NOTE: This last part was an area I was lightly involved in compared to the other two due to my other obligations but I still provided my feedback to the rest of the team).

These investigative audits, explorations, and frameworks helped our team present different options and potential outcomes to executive leadership and get their feedback on the best approach to take as well as their support in unblocking us so we could continue delivering services that could continue to help our customers. We also continued to use this as a means of showing our progress as we continued to launch our experiences.

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DEVELOPING A SHARED STRATEGY TO A BETTER WORLD

A LEARNING PLAN TO VALIDATE AND DERISK

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PROJECT TIMELINE

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AN ITERATIVE DESIGN PROCESS

As the co-founder and Design Lead of the QuickBooks Contractor Ecosystem, I had been involved in a total of 3 launches, 2 vision prototypes, and iterating on the experience through numerous explorations and prototypes. Because we were covering 3 distinct touchpoints for a dual-stakeholder journey across multiple different QuickBooks products, we were simultaneously designing experiences for 6 key product areas: Onboarding, Invoicing & Payments, and Tax Time.

As a Design Leader, I drove the op mechs, directed and coordinate our collective team efforts, developed our team structures and processes, gathered and shared resources, delegated work, and mentored the design team. While I focused on the core experience alongside a visual designer and a part-time content designer, I had the other designers do deeper dives in areas such as Payroll Activation (which enabled contractor direct deposits), how contractor payments were viewed in the Contractor Center, how a contractor could send their tax information to TurboTax once they were ready to file taxes, developing relevant help articles, and creating the marketing assets necessary to communicate these new contractor-friendly capabilities.

As a hands-on designer who had the big picture view and scope for what we wanted to deliver with each progressive launch, I primarily focused on developing the core structure of the experience as well as the key use cases we prioritized. For each touchpoint, I developed flow maps, wireframes, higher-fidelity visual screens that leveraged our design system assets, reviewing the designs with key stakeholders, gathering feedback from target customers, developing rapid prototypes, and delivering specced-out assets to our build partners. To do this hands-on design work, I used the following tools:

Wireframes and Visuals: Sketch, Figma, Illustrator, Photoshop
Prototyping: Figma, Invision, Adobe XD
Research Studies: Indesign, Invision, Sketch, Figma, and Mural
Design Team Collaboration: Abstract, Sketch
Delivering Final Assets to Build Partners: Zeplin

By being able to balance my role as both a Design Leader and a hands-on designer, I was able to direct our team of designers across multiple simultaneous workstreams while remaining tightly coordinated. Working in this manner also enabled me to ensure that as our experiences evolved, those changes were consistently updated throughout the ecosystem.

ContractorEcosystem_AllFlows_RecentThinking2018_Figma.jpg

PREVIEW AT QUICKBOOKS CONNECT IN 2017

Each year, QuickBooks organizes QuickBooks Connect for business and accounting professionals to connect with each other, learn new ways to move their business forward, and announce upcoming features.

Since our team was still a few months away from launching v1 of the QuickBooks Contractor Ecosystem, executive leadership granted us a small stage at QuickBooks Connect which we leveraged to announce our upcoming features and getting a quick round of feedback. We presented an early, stripped-down prototype that demonstrated the flow of data. We also flew in a small panel of small business owners, accountants, and contractors to share their perspectives—some of whom had previously provided feedback on our earlier designs and understood our goals.

Overall, QuickBooks Contractor Ecosystem was very well received and our team was able to collect valuable feedback in a relatively short duration of time. We had attendees who expressed wanting to immediately use this ecosystem to finally distinguish between the contractors that had been getting mixed into their vendors’ list. Others wanted this to be launched in time for tax season so they could use it to securely e-file and e-deliver 1099-MISC tax forms to their Self-Employed Contractors.

In this video, you can view the first time an early version of QuickBooks Contractor Ecosystem was presented to a small, public audience. I drove the development of this prototype in collaboration with a Design Technologist.

ONBOARDING MLP

INVOICING & PAYMENTS

TAX TIME MLP

PROJECT RETROSPECTIONS

Whenever I reflect about my time on this project, I am filled with immense pride about what our team was able to accomplish in a relatively short amount of time despite the seemingly endless challenges that lay in our path. I especially light up when I’d hear unsolicited feedback from customers about how those features have made lives easier for them and those with whom they work because it reinforces the value of thinking collectively and systematically about our customers, as opposed to superficial business-influenced boundaries.

However, I am also able to recognize the many opportunities for improvement. If I had the chance to do this project over knowing what I now know, here are a few key areas I would have pushed harder to do differently.