When a founder who already controls the voting power of a company still buys millions of dollars’ worth of stock on the open market, investors should ask why.
Between 11 July and 24 July 2025, Asana co‑founder Dustin Moskovitz scooped up 897,000 Class A shares at roughly $14‑$15 apiece under a 10b5‑1 plan, putting another $13 million of his own cash on the line.
That kind of conviction from someone who already owns more than 57 million shares and commands majority voting control is impossible to ignore.
What the Quarters Don’t Shout From the Headlines
Asana crossed two under‑the‑radar milestones this spring, the first being positive non‑GAAP operating margin (4% in Q1 FY26).
The second is first quarter of positive free cash flow just four months earlier (Q4 FY25).
The shift from burning cash to generating it happened a full year ahead of most sell‑side models published in 2024.
That speed matters because software valuations expand almost automatically once companies prove they can fund their own growth.
High‑Margin Machine Hiding in Plain Sight
Despite the modest revenue growth rate of 9% year over year last quarter, Asana’s gross margin hovers near 89%, among the fattest in the collaboration‑software cohort.
Why isn’t Wall Street paying up? Because at $15 a share, Asana trades for 4.7x trailing‑12‑month revenue, less than half of Monday.com’s 14.8x and Atlassian’s 10.5x.
If Asana merely closed half of that gap, the stock would already be within striking distance of $30.
The Optionality Most Models Skip
Last year Asana rolled out AI Studio, a usage‑based add‑on that lets customers build no‑code AI “agents” inside their workflows.
Management disclosed that AI Studio raced past $1 million in annual recurring revenue during its very first quarter on the market.
Because AI Studio is sold on a consumption model rather than per‑seat licenses, it can lift revenue without expanding headcount, a lever most coverage models, still seat‑based, have not incorporated.
Competitive Chessboard
The work‑management arena is crowded, but the field is splitting into price‑led generalists and premium workflow engines.
Microsoft Planner, bundled in Office 365, caps the low end. Monday.com and Atlassian’s Jira tilt toward developer and product teams.
Asana is positioning itself as the human + AI coordination layer and doing so at roughly one‑third the valuation of its peers, per the price‑to‑sales numbers above.
That mis‑pricing exists largely because headline revenue growth slowed to single digits. If AI Studio and Smart Workflow Gallery (a slate of pre‑built AI templates launched in May) rekindle expansion to even the mid‑teens, valuation math changes fast.
Leadership Shuffle, a Risk or Catalyst?
In June Asana announced that Dan Rogers, former LaunchDarkly and ServiceNow executive, will succeed Moskovitz as CEO on 21 July 2025.
Rogers is a go‑to‑market specialist credited with scaling ServiceNow from $350 million to $4 billion in cloud revenue and tripling LaunchDarkly’s ARR in three years.
His playbook tends to revolve around large‑account upsells, precisely where Asana’s net‑retention rate (NRR) just hit a soft patch.
Management warned that Q2 NRR could dip below 95% as tech customers trim seat counts. A CEO who lives and dies by ballooning revenue arriving when NRR is under pressure could become an accelerant rather than a headwind.
Another factor is early‑stage software names often rely on stock‑based compensation, diluting investors faster than revenue accrues.
Asana is bucking that trend. In March the board authorized a $150 million buyback, roughly 4% of shares outstanding at current prices.
Combine that with chronic insider accumulation and net dilution could turn negative as soon as FY27, a rarity among sub‑$5 billion SaaS firms.
What Would It Take to Hit $30?
Below is a back‑of‑the‑napkin framework, not a forecast:
If Asana exits FY28 at $910 million in revenue and a 15% operating margin, a 9× forward sales multiple, still a discount to Monday.com today, implies a $8.2 billion enterprise value.
Subtracting ~$250 million net cash leaves $7.9 billion equity value, or ~$32 per share, a clean double from current levels. Even a middling 6× multiple lands just under $22.
What Could Break the Thesis?
If large‑seat customers consolidate onto Microsoft 365 or Atlassian, revenue could stagnate despite new products plus there’s a culture shock risk under a go‑to‑market CEO can spark turnover.
If every rival bundles comparable AI agents for free, AI Studio’s pricing power fades.
Little‑Known Levers That Could Surprise to the Upside
Channel partners are lining up to become AI Studio‑certified integrators, expanding the salesforce without adding payroll.
Dual‑class structure means strategic pivots face no shareholder gridlock. Moskovitz retains majority vote, so bold bets, or a sale, need no proxy fight.
On a bullish note, Asana ended Q1 with more cash than total liabilities, rare for a company still labeled “unprofitable.”
Best of all, gross‑margin headroom is extraordinary. At 89%, incremental revenue drops almost straight to operating profit, accelerating EPS once growth re‑accelerates.
Will Asana Stock Double?
The path is neither automatic nor risk‑free, but the ingredients for a double are in the pantry, including being valuation already discounting tepid growth and operating leverage is emerging a year early.
So too a consumption‑based AI product offers an under‑modeled upside vector and insider buying and a buyback cap downside dilution.
A revenue‑expansion specialist is taking the helm precisely when expansion metrics wobble, timing that could read like destiny in hindsight.
Let’s see will Rogers push growth back into the mid‑teens and prove AI Studio is more than a buzzword, the market is likely to reward Asana with a peer‑level multiple. Under that scenario, $30 a share is less pie in the sky than a valuation catch‑up play.
Bottom Line
At today’s sub‑$4 billion market cap, Asana offers investors a cheap ticket to two shows, including a possible demand revival in a still‑scorching collaboration market and a second‑act AI monetization story.
Neither is guaranteed but when the founder keeps writing eight‑figure checks and the board deploys cash to buy back stock instead of printing new shares, the odds of investors seeing a double look better than the ticker’s sleepy chart suggests.
The author has no position in any of the stocks mentioned. Financhill has a disclosure policy. This post may contain affiliate links or links from our sponsors.