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Outgrowing Smartsheet.

Moving complex work to Jira, at your pace and without the risk
by Dave Rosenlund

About the Author

Dave Rosenlund

Trundl

Global Head of Software & Solutions
Atlassian Community Champion
Dave Rosenlund is Global Head of Software & Solutions at Trundl, a Platinum Atlassian Solution Partner | Enterprise, and an Atlassian Community Champion. He writes about what it takes to make AI and service management work in real enterprise environments, including the AI That Works and Beyond ITSM series in the Atlassian Community.

About Trundl

Trundl is a Platinum Atlassian Solution Partner | Enterprise. It pioneered Contextual Delivery: instead of starting from workshops and templates, Trundl starts from what a company already has, its current systems, its process documents, and the way its teams do the work. Trundl also built Rapid Deploy, the engine its architects use to turn that context into a working environment the people who will use it can see and validate before anything cuts over.

Executive Summary

01 Executive summary

Smartsheet earned its place, and for a lot of work it still fits. But in many organizations, the plans live in Smartsheet while the delivery work behind them lives in Jira, run by related but separate parts of the business. Programs cross teams, regions, and tools, and leaders expect AI working inside the work itself. That's where a spreadsheet-style tool starts to strain, and where the real cost of staying gets harder to see.

A hand holding up a pair of binoculars

Most teams don't stay because they prefer Smartsheet. They stay because moving to Jira looks risky. Take the risk out of that move, and the decision changes. At Toshiba Global Commerce Solutions, eight teams had a working Jira built from their own requirements within hours of their second meeting, and were testing it before anyone committed to a cutover.

This paper shows what that kind of move looks like, and closes with a readiness check and a business-case frame to use before your next renewal.

Most teams don't stay because they prefer Smartsheet. They stay because moving looks risky.

At a glance, three numbers

  • 85%

    of the Fortune 500 use Smartsheet

  • 130→10

    hours to build Toshiba's Jira (scoped vs actual)

  • 20,000

    row cap per Smartsheet sheet

The case for change from Smartsheet

Why staying on Smartsheet is becoming the riskier choice

A hand holding up a Rubik's cube

Smartsheet earned its place

Here's a conversation I've seen more than once. A budget review gets to the software line, and someone asks why the company pays for two work platforms: one where engineering tracks delivery, and one where the PMO runs the plan. The answer comes back fast. “Smartsheet works for us.”

It's usually true. Smartsheet looks and feels like a spreadsheet, which makes it familiar from the first day. Smartsheet says 85% of the Fortune 500 use it. Its users mostly like it: it holds a 4.4 out of 5 from more than 22,000 reviews on G2. And Gartner named it a Leader in its 2025 Magic Quadrant for Collaborative Work Management, alongside Atlassian.

Smartsheet is a good product, and the people who built on it built real systems: templated programs, cross-sheet formulas, rollup dashboards, earned-value reports a steering committee trusts. The more useful question is what all of that is now being asked to carry. In many organizations, the answer includes a connection to delivery work that lives in Jira, maintained through a connector or by hand, and growing harder to keep in step.

The work changed underneath it

Today's work spans more teams, more regions, and more tools than it used to. Plans depend on work tracked somewhere else, most often in Jira, where engineering and IT already run their delivery. Leaders want a single portfolio view, and they increasingly expect AI to help inside the work itself.

That puts pressure on a spreadsheet-style tool in ways you can check for yourself.

Start with the sheet. Smartsheet caps each sheet at 20,000 rows, 400 columns, and 500,000 cells, and several features, including the Power BI and Tableau connectors, aren't supported on sheets over 5,000 rows or 200 columns. Complex programs get around this by spreading across many linked sheets, which is where cross-sheet references, reports, and manual reconciliation start to pile up.

The packaging is where the cost of staying hides. Portfolios and Scenario Planning are Enterprise-plan features. A portfolio-scale PMO relies on dashboard rollups, data integration, and connectors to other systems. Much of that sits in a premium layer, priced separately or bundled into Smartsheet's top tier, often quote-only. For teams already on Jira, Smartsheet's Jira Connector is a paid premium offering that supports one connector workflow per sheet. None of that shows up in the per-seat list price, and neither do the hours people spend stitching sheets together and building status reports by hand.

Then there are the users. The single most-tagged complaint on G2 is a steep learning curve, though no tool, Jira included, is effortless at scale. Close behind it are missing features, limited features, and limited customization. Check those against your own experience.

None of this is a flaw for simple work. A team tracking a few dozen tasks will never hit these limits, and it shouldn't move. Running Smartsheet and Jira side by side, with a connector between them, can also be the right call when only a few plans touch delivery work. It gets harder to sustain as more plans depend on Jira, because every sheet needs its own sync and someone has to own it. These signs become the readiness check at the end of this paper.

Where the sheet runs out

Smartsheet limits per sheet: 20,000 rows, 400 columns and 500,000 cells. Power BI and Tableau connectors stop above 5,000 rows or 200 columns.

Sources: Smartsheet Help Center, 2026

The bet changed, too

There's a second thing a senior leader should weigh before the next Smartsheet renewal, and it has nothing to do with features. It's the company behind the product.

I'll stick to dated facts here, because this is the part of the story that's easiest to overstate.

Smartsheet, as of November 2026

Blackstone and Vista Equity Partners took Smartsheet private in January 2025 for $8.4 billion. In the nine months after the deal closed, Smartsheet had three CEOs: its longtime chief executive retired in August 2025, an acting CEO followed, and a new CEO started in October 2025. The company cut staff in October 2025 and again in February 2026.

Smartsheet also changed how it licenses. Under its user subscription model, provisional members, people who get free access for up to 90 days, are automatically converted to paid members unless an administrator reclassifies them. Annual plans moved to this model at their first renewal after January 1, 2025, so many customers renewing in late 2026 are on their second renewal under it. Smartsheet says customers who transitioned see, on average, about 70% more seats for less than a 10% increase in fees, and its loyalty pricing holds for customers who maintain or increase their spend year over year.

Smartsheet announced its own AI agents in November 2025. As of November 2026, they're listed as “coming soon,” with an early adopter program.

Every line in that box is checkable, and none of it means Smartsheet is going anywhere. Plenty of private-equity-owned software companies serve their customers well. But a leader signing a multi-year commitment should know who owns the vendor, how the licensing behaves, and where the roadmap stands. What those facts mean for your organization is your call.

The same scrutiny belongs on any platform you renew, Atlassian included. Know which features your plan tier includes; in Jira, cross-project planning requires a Premium or Enterprise plan. Know how AI usage is metered; Atlassian includes a monthly allowance of AI credits with its paid plans and, as of November 2026, is scheduled to begin billing for usage beyond that allowance on December 3, 2026. A fair comparison puts both vendors in the same box.

The barrier and the better move

Why teams stay, and what a move that takes the risk out looks like

Why teams stay anyway

When I ask teams why they're still on Smartsheet, I rarely hear that they love it. I hear something closer to this. “We've built too much here.” “Our PMO works this way.” “We can't pause active projects.” “We'd have to rebuild everything.”

Behind all four sits a fifth reason nobody says out loud. The person who champions a migration that goes badly pays for it, professionally. If the move stalls, or a quarter's reporting breaks, or the PMO revolts, it's the champion's name on the slide. Staying is the safer bet for the individual, even when it isn't for the organization.

A hand lifting two glass cubes, each holding a cloud, one above the other

Staying is the safer bet for the individual, even when it isn't for the organization.

Those fears are reasonable, and the standard path out does little to calm them. Jira can import from several tools, but it has no dedicated Smartsheet importer. The native route is a CSV upload. Rows come across. The formulas, hierarchies, dependencies, and working practices teams rely on don't. The team ends up rebuilding by hand what took years to grow, while still running the old system for the work in flight.

Look closely at what people are afraid of. Some of it is Jira itself, especially for business users, and that deserves an answer later in this paper. But most of it is the move: losing history, breaking reporting, stalling active work.

That is a different problem, and it has a different answer. So why should migration be the thing that slows down an organization's ambition? Change the move.

What a better move looks like

A move worth putting your name on has four properties. None of them is exotic, and together they take most of the risk out.

A better move, in four steps

  1. Built from your own work

    Your sheets, documents and structures are the input.

  2. See it before you commit

    A working config goes in front of your people in a test environment.

  3. Move in stages

    Teams move in waves, both systems kept in sync, no stop-work weekend.

  4. You own the result

    Standard Jira in your own instance, no dependency on the partner.

Start from your own work. The sheets, the process documents, the requirements conversations, and the structures your teams already use are the input. The new environment is built from how your organization works today, so people recognize it the first time they log in.

See it working before you commit. A working configuration, built from your own context, goes in front of the people who will use it while there's still time to change it. If it doesn't fit, you find out in a test environment, well before cutover.

Move in stages, without stopping your work. Teams move in waves while the old system and the new one are kept in sync, one way or both ways as the project needs, so active projects keep running where they are until it's their turn. Portfolio reporting continues throughout, and nobody bets the quarter on a single weekend.

Own the result. What you end up with is standard Jira, configured in your own Atlassian instance and run by your own admins. Once the last team has moved and the old system is retired, nothing about it depends on the partner who built it.

A good move is also plain about two things. The first is what it asks of your people: the heaviest lift is time from the people who know how the work runs today, and then time to test what's built. The build itself shouldn't be theirs to carry.

The second is cost. Plan for Jira Premium or Enterprise wherever you need portfolio planning, a Marketplace app if you need earned value, and the partner's work. Weigh that against the renewal, the add-ons, and the hours spent keeping two systems in step.

Rebuild the work on one platform

I've written before that a migration is the moment to rethink how work runs, beyond simply moving it. Copying today's sheets into a new tool carries the mess along with the data. The better move is to keep what works and reimagine what doesn't, and to build AI into the rebuilt workflows as a working participant, on a platform your organization owns and can keep evolving.

Ownership is the hard part. In September 2026, Gartner predicted that by 2028, 70% of enterprises will abandon agentic AI built for them by a vendor's own engineering teams, “trapped by soaring costs and unable to evolve it on their own.” Gartner's advice is to make sure “the solution reflects how work actually gets done,” and to measure success by the enterprise's own ability to manage and adapt the technology. That applies to any partner, including the one helping you move. AI has to live where the work lives, and it has to belong to the customer.

The platform where your delivery already runs can carry that AI. Jira lets teams assign work items to AI agents, mention them in comments, and build them into workflows. That includes agents from Rovo, Atlassian's AI, and third-party agents connected through the Model Context Protocol (MCP), an open standard for linking AI tools to business systems. Those agents work inside the controls you already have: they can only see or act on information the user already has permission to see, admins decide who can create them, and their activity shows up in the audit log. Smartsheet's own agents, by comparison, are still in early access.

If your delivery already runs in Jira, this is the heart of the case for consolidation. Today your plans live in one system and your delivery in another, with a paid connector or a person in between. Bring them together and you get one platform, one set of controls to govern, and one vendor to renew. Most of all, you get AI that can work across the plan and the delivery behind it, under one permission model. Smartsheet has done useful work here, too: its MCP server lets outside AI tools reach Smartsheet data. Rovo can reach Smartsheet, but its connector only indexes the sheets, so it can't read the rows inside them. The agents your teams are starting to use in Jira can find a plan, but they can't act on what it says.

One platform vs two

Two systems: plans in Smartsheet and delivery in Jira, tangled together by a paid connector or a person in between
One platform: plans, delivery and AI together under one permission model

If you don't run Jira yet, the same logic applies with one more step: the case is a platform that can carry business planning, delivery, and portfolio views together, instead of another point tool to integrate. That's a bigger decision, and it deserves its own comparison of the platforms you're considering.

Who is this for?

Answering the objection for the PMO that decides whether the move happens

A hand balancing a spinning pen on one fingertip

What the PMO needs to hear

If you lead a PMO, you've probably read this far with some skepticism. That's fair. You built the system that works, and your name is on whatever replaces it. Here's what I'd want to know in your seat, and what a good move should tell you.

Your structures can carry over. A move doesn't have to mean adopting someone else's template. The hierarchy you run programs with today can be the hierarchy you run them with tomorrow. Each piece of what you built needs a named equivalent, agreed up front. Control Center program templates become project templates and automation. Cross-sheet formulas become calculated fields, automation, or a Marketplace app. Rollup dashboards become Jira dashboards and Plans.

Your history doesn't have to disappear. Historical data can move with you, or the old sheets can stay available, read-only, as the record. Earned-value baselines need the same decision: carry them across, or close them out at cutover and start new baselines with a documented reconciliation. Make that call before the first team moves, and make sure someone owns the numbers if the two systems disagree during the transition.

Your business users deserve a real test. This is the objection I hear most. Jira is no longer only an engineering tool: business teams work in list, board, calendar, and timeline views, the list view supports inline editing, and Atlassian ships ready-made spaces for work such as marketing campaigns, hiring, budget tracking, and event planning. But inline editing isn't a spreadsheet formula, and your finance users will notice. Don't take my word for it, or Atlassian's. Put your least technical users in front of a working version of their own work, and let them tell you. Plan for enablement either way.

Earned value gets an honest answer up front. Jira doesn't do earned-value management natively. It comes from Marketplace apps or an agreed reporting method, and that choice should be made at the start, well before month three. Budget for the plan tier, too: portfolio planning in Jira requires Premium or Enterprise, much as Portfolios does on Smartsheet.

And there's a gain worth naming. When plans and delivery live in the same system, the PMO no longer has to reconcile two sources of truth. Status still depends on people keeping their work current; no platform fixes that. But it comes from one place, and the PMO's time can go to acting on the picture instead of assembling it.

Smartsheet → Jira

Smartsheet to Jira, mapped

In Smartsheet: Control Center program templates, cross-sheet formulas, rollup dashboards In Jira: project templates and automation; calculated fields, automation, or a Marketplace app; Jira dashboards and Plans

Evidence from what Toshiba did

What the move delivered for one customer

Toshiba saw it before committing to it

Toshiba Global Commerce Solutions moved eight teams, 83 people, off Smartsheet and into its corporate Jira. What matters most is when they first saw it. Working from Toshiba's own requirements meeting transcripts and work-breakdown documents, Trundl's architects used Rapid Deploy to deliver a working configuration in a test environment within hours of the second meeting. The teams were testing their own Jira, with their own structures, before anyone committed to a cutover.

A hand holding a coiled spring toy

Trundl's case study credits those familiar structures with lowering change resistance. Leaders had portfolio-level rollups from the test environment onward, with earned-value management and capacity planning supported from the start. Earned-value tracking came from Marketplace apps, including Tempo, configured into Toshiba's Jira. The build itself had been scoped at about 130 labor hours and took about 10.

Toshiba

Trundl is leveraging AI in innovative ways. We anticipated months to build a custom Jira solution for a new development process, but Rapid Deploy analyzed our requirements meeting transcripts and delivered a sandbox-ready configuration within hours of our second meeting.

Jim Hawk

Toshiba Global Commerce Solutions

Toshiba chose to start fresh rather than bring historical data across; moving data was available and remains an option. The hours describe the build itself. The full rollout, through testing and into production, moved at Toshiba's pace.

Scoped versus actual: 130 labor hours scoped, about 10 actual. 8 teams, 83 people.

A word on your data

Security teams ask about this first. Trundl is certified to ISO 27001:2022 and holds a SOC 2 Type II attestation. Customer data is never used to train AI models. Trundl's tooling is kept separate from customer data, access during an engagement follows least-privilege principles, and nothing is automated in a customer's environment without people validating and approving it. The details, including how Rapid Deploy accesses, processes, and stores customer data, are in Trundl's Rapid Deploy and Customer Data Policy, available through its Trust Center.

Before you decide, ask

Why the renewal is the moment, and the questions to ask

A hand holding up a horseshoe magnet

The questions to ask before you renew

Two things make a renewal the right moment to decide, and both come around every year.

The first is the budget calendar. About seven in ten US public companies close their fiscal year in December, and so do a majority of Canadian public companies. In India, the financial year ends March 31 by law. Budgets lock on a predictable schedule, and a decision made before next year's budget locks is far easier than one made after.

The second is the renewal itself. A Smartsheet renewal now comes with conditions, from seat conversion to spend-dependent loyalty pricing. You'll be asked to commit again whether you've looked at alternatives or not.

If your renewal is only a few months away, you probably can't move everything before it, and you don't need to. Use the time to see a slice of your own work running in Jira and to plan the waves. Then look at the terms: a shorter commitment may cost more per seat, and reducing spend can affect Smartsheet's loyalty pricing, but either may be worth it if you know you're moving.

So I wouldn't start with “should we leave Smartsheet?” I'd start here: will you sign the next renewal without first seeing your own work running in Jira?

Will you sign the next renewal without first seeing your own work running in Jira?

And it goes one step further. The tools you chose when the work was simpler won't necessarily be the tools that carry it through the next five years of AI, consolidation, and growth. Each renewal decides, for a few more years, where your plans live, and whether the AI your teams use for delivery can work with them.

How to get started

Start with the readiness check in the appendix. It's built to tell you honestly where you stand, including when the answer is “not yet.”

If the answer is anything else, the next step is to see it working before you commit to anything. Trundl's architects can take a slice of your current Smartsheet setup, rebuild it in Jira with your structures and terminology intact, and put it in front of the people who would use it. You decide what happens next with something real in front of you.

To see what that looks like, watch the walkthrough: a Smartsheet setup rebuilt in Jira, the PMO's views preserved, and both systems kept in sync during a staged move.

Checklist: Assess if you're outgrowing Smartsheet

A self-contained readiness check and a business-case frame

Part 1: The readiness check

The signs. Answer each question yes or no. Be honest. The check only works if it can tell you to wait.

A hand holding up a glass cube with a cloud inside

  1. Do any of your sheets run past 5,000 rows, where some Smartsheet features stop working?

  2. Does keeping linked sheets consistent take someone's regular, recurring time?

  3. Are you paying for top-tier plans or add-ons largely to work around limits?

  4. Do you pay for, or manually maintain, a sync between Smartsheet and your other tools?

  5. Do plan dates slip because delivery status in Jira, or another tool, isn't reflected in Smartsheet in time?

  6. Do teams in different regions or business units keep their own copies of the same plan?

  7. Does your PMO spend hours each month assembling status reports by hand?

  8. Have you tried to get AI to work across your plans and the delivery work behind them, and hit a wall?

The bands below are a rough guide.

0 to 2 yes

Not yet

Smartsheet still fits your work. Come back to this check as your programs grow.

3 to 5 yes

Worth a look

Some of your work has outgrown the grid. See it running in Jira before you sign again.

6 to 8 yes

Time to plan the move

Your work has outgrown the tool. The question now is how to move without disrupting it.

The timing. If you scored 3 or more, these tell you how soon to act. Is a Smartsheet renewal coming up in the next six months? Is next year's budget being set? Is your organization already consolidating tools, or using Atlassian for other work? Each yes is a reason to start sooner.

Part 2: The business-case frame

If you already believe it's time, the harder job is often convincing the people above you. Use these five headings to build the case on outcomes.

  1. The risk of staying

    Which facts from “The bet changed, too” apply to your renewal? What does your contract commit you to, and for how long?

  2. The cost of staying

    Count the premium tiers and add-ons, the sync you pay for or maintain, and the hours spent reconciling sheets and building reports by hand.

  3. What changes

    Describe one connected system: strategy traceable to delivery, a portfolio view leaders trust, and AI working inside the flow of work, under your own governance.

  4. How the risk is controlled

    Built from your own work. Seen working before you commit. Moved in stages while both systems stay in sync. Owned by you when it's done.

  5. The ask and the timing

    Name the decision you need, who makes it, and the date it has to be made by, tied to your renewal and your fiscal year.

References

  1. [1] Smartsheet press release on Intelligent Work Management, Business Wire, November 5, 2025. https://www.businesswire.com/news/home/20251105764524/en/
  2. [2] G2, Smartsheet reviews and tagged pros and cons, checked September 29, 2026. https://www.g2.com/products/smartsheet/reviews?qs=pros-and-cons
  3. [3] Atlassian announcement of the 2025 Gartner Magic Quadrant for Collaborative Work Management. https://www.atlassian.com/blog/announcements/gartner-collaborative-work-management
  4. [4] Smartsheet Help Center, system requirements and guidelines, checked September 29, 2026. https://help.smartsheet.com/articles/506775-system-requirements-for-using-smartsheet
  5. [5] Smartsheet, Plans and pricing, checked September 29, 2026. https://www.smartsheet.com/pricing
  6. [6] Smartsheet Help Center, Jira Connector FAQ, checked September 29, 2026. https://help.smartsheet.com/articles/2482656-jira-connector-faq
  7. [7] GeekWire, on the close of Smartsheet's take-private, January 2025. https://www.geekwire.com/2025/smartsheet-officially-goes-private-completes-acquisition-by-blackstone-and-vista-equity-partners/
  8. [8] GeekWire, on Mark Mader's retirement as CEO, August 5, 2025. https://www.geekwire.com/2025/smartsheet-ceo-mark-mader-retiring-apptio-co-founder-sunny-gupta-will-take-over-enterprise-giant/
  9. [9] GeekWire, on Raj Singh's appointment as CEO, October 6, 2025. https://www.geekwire.com/2025/raj-singh-named-smartsheet-ceo-returning-to-his-enterprise-software-roots-in-the-seattle-area/
  10. [10] GeekWire, on Smartsheet's February 2026 layoffs, which also reports the October 2025 reduction. https://www.geekwire.com/2026/smartsheet-layoffs-enterprise-software-giant-cuts-staff/
  11. [11] Smartsheet, customer loyalty benefit and seat-type update, June 2025. https://www.smartsheet.com/content-center/product-insights/product-updates/smartsheet-customer-loyalty-benefit
  12. [12] Smartsheet Help Center, System Admin guide to the user subscription model migration. https://help.smartsheet.com/articles/2483341-system-admin-guide-migration-user-subscription-model
  13. [13] Smartsheet, AI, checked September 29, 2026. https://www.smartsheet.com/ai
  14. [14] Atlassian Support, Plans in Jira Cloud. https://support.atlassian.com/jira-software-cloud/docs/what-is-advanced-roadmaps/
  15. [15] Atlassian Support, Rovo usage limits, checked September 29, 2026. https://support.atlassian.com/rovo/docs/rovo-usage-limits/
  16. [16] Atlassian Support, importing data into Jira. https://support.atlassian.com/jira-software-cloud/docs/import-data-into-jira/
  17. [17] Dave Rosenlund, “Migration to Atlassian Cloud is the Perfect Time to Transform | Rovo Can Help,” Atlassian Community. https://community.atlassian.com/forums/Rovo-articles/Migration-to-Atlassian-Cloud-is-the-Perfect-Time-to-Transform/ba-p/3195993
  18. [18] Gartner, “Gartner Predicts 70% of Enterprises Will Abandon Agentic AI Built by Vendor Forward-Deployed Engineering by 2028,” September 29, 2026. https://www.gartner.com/en/newsroom/press-releases/2026-09-29-gartner-predicts-70-percent-of-enterprises-will-abandon-agentic-ai
  19. [19] Atlassian, announcement of agents in Jira, February 25, 2026. https://www.atlassian.com/blog/rovo/ai-agents-in-jira
  20. [20] Atlassian Support, Rovo agent permissions and governance, checked October 2, 2026. https://support.atlassian.com/rovo/docs/rovo-agent-permissions-and-governance/
  21. [21] Atlassian, Rovo security, privacy, and data use, checked October 2, 2026. https://www.atlassian.com/software/rovo/guides/admin-guide/rovo-data-usage-privacy
  22. [22] Atlassian Support, Connect Smartsheet to Teamwork Graph, checked October 2, 2026. https://support.atlassian.com/organization-administration/docs/connect-smartsheet-to-rovo/
  23. [23] Atlassian, “Jira goes where spreadsheets can't,” August 25, 2026. https://www.atlassian.com/blog/development/planning-and-budgeting-in-jira
  24. [24] Trundl, Toshiba Global Commerce Solutions case study. https://trundl.com/case-studies/toshiba-global-commerce-solutions-rapid-deploy-jira/
  25. [25] Trundl, Trust Center, checked October 2, 2026. https://trundl.com/trust-center/
  26. [26] Numeric, analysis of 717 public companies, January 2025; consistent with Audit Analytics (about 71%), 2015; Canada: Audit Analytics (nearly 57%), 2019.
  27. [27] India, Companies Act 2013, Section 2(41). https://indiankanoon.org/doc/34358949/

AI tools helped research, develop, draft, and refine this piece. The ideas, structure, judgment, and responsibility for what it says belong to the author. AI helped get past the blank page and supported the work that followed. The thinking is human.

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