Vic Chynoweth is the CEO of Tempo, a strategic portfolio management platform used by more than 30,000 organizations, including a large share of the Fortune 500. A biology undergrad who found his way into finance, Vic built his career on the operating side of software companies, with CFO and COO roles at Planview and JAGGAER, multiple leadership roles at Cray, and a turn as Managing Director and Operating Partner at Cove Hill Partners before taking the CEO seat at Tempo in 2025. He describes himself as a framework- and principles-led leader.
Episode Description
What if the reason software valuations are falling apart has nothing to do with cost structure and everything to do with a single line in a discounted cash flow model?
Vic Chynoweth came up through finance, not engineering, and that vantage point gives him an unusual but valuable perspective for this show. In this episode, he gives us a crash course on the concept of durable right to win and answers why AI putting that in question is enough to vaporize the terminal value that carries most of a high-growth software company’s valuation. It is the clearest explanation of the so-called SaaS-pocalypse you’re likely to hear, delivered by someone who has to lead a company through it.
From there, the conversation turns to practical leadership. Vic lays out the leadership axioms he introduces on his first call with a new company, why he thinks his job is to make himself unnecessary, and the four categories of work (architecture, orchestration, builder, and field operations) he is currently using to rethink human capital management from scratch. He and Dave dig into where the delivery bottleneck went once AI removed it, why attribution between human and agent work is becoming a first-class measurement problem, and how to automate change management so the system doesn’t create developer whiplash every five minutes.
There is also a nice segment on org design as a continuous experiment rather than an annual reorg, an honest postmortem on why monolithic portfolio management implementations made everyone miserable, and Vic’s argument that employee engagement is the single most important metric at a software company. Not because it’s a nice vibe, but because it is one of the very few measures where the professional and personal wins point in the same direction.
Links and Resources
Guest Links
Tempo Software, the strategic portfolio management platform Vic leads
Vic’s Forbes Technology Council profile, which lays out his leadership axioms
Tempo’s announcement of Vic as CEO (January 2025)
Films and Articles Mentioned
The Thinking Game (2024), the documentary on Demis Hassabis and Google DeepMind that Vic and Dave both watched recently. It centers on AlphaFold solving the protein folding problem, and is free on YouTube
Anthropic on Project Glasswing and Claude Mythos Preview, context for Vic’s point that security is his biggest AI concern
Dario Amodei’s warning on entry-level white-collar work, the Anthropic CEO comments Vic references
Tools, Frameworks, and Concepts
Durable right to win, a company’s long-term sustaining ability to generate cash flow, and the thing Vic argues AI has thrown into question across software
Terminal value, the perpetuity assumption at the end of a discounted cash flow model, and where most of a high-growth software company’s valuation actually lives
Vic’s leadership axioms, in order: visibility and alignment, accountability and support, enable and empower
Vic’s scalability principles: simplify, standardize, consider the customer experience, sustainability
Vic’s four categories of work: architecture, orchestration, builder, field operations
Vic’s definition of attribution, measuring the economic value of putting a person versus an agent versus both on a piece of work
Strategic Portfolio Management (SPM), the category Tempo competes in, project portfolio management (PPM)
Jevons paradox, raised by Dave in the context of AI creating new categories of work. Worth noting that Amodei himself reached for the same framework in 2026
Systems of record versus point solutions, Dave’s framing for which software businesses have a data moat and which are in the crosshairs
Forward-deployed engineers, a role originated by Palantir, Vic notes nobody was discussing a year ago, and everyone is discussing now
Planview, where Vic served as EVP and CFO, and a major player in traditional PPM
Atlassian and Jira, the ecosystem Tempo has historically built on, plus Linear, one of the ecosystems it is expanding into
Build, measure, learn, invoked by Dave as the loop that becomes essential again once shipping stops being the constraint
People Referenced
Dario Amodei, CEO of Anthropic, on AI displacing early career roles in technology: a prognostication he’s since walked back on but continues to bubble up in the conversation
Demis Hassabis and Google DeepMind, via The Thinking Game
Marie-Michèle Caron, Tempo’s Chief Revenue Officer
Kevin Nanney, Tempo’s Chief Product Officer
Shams Chauthani, Tempo’s Chief Technology Officer
Topics Discussed
From Biology to Finance to the CEO
Vic opens by acknowledging that the path from biology undergrad to software CEO is not exactly a straight line. What connects the dots is a self-assessment he made early on: he is adequate as an entrepreneur but much better at scaling enterprises. Cray came first, one of the hardest and best experiences of his career, followed by private equity software, and then a run of CFO and COO roles.
Key points:
Starting a company between undergrad and grad school taught him less about entrepreneurship than about the difference between what he prefers and what he is merely adequate at
Finance is what he calls a “connected organization,” with an open door into every function, which forces you to go find where you can add value
The single most important thing that role taught him was empathy: asking what he would need to make decisions if he were the CRO, the CTO, or the CIO, then bringing exactly that to the table
His formative habit is delivering data in the right form at the right time, usually visually, because up and to the right is legible in a way that rows and columns are not
Leadership Axioms and the Goal of Not Being Needed
Asked how to get a leadership group functioning as an actual team rather than treating teamwork as a contributor-layer concern, Vic reaches for the three axioms he introduces on his first call with any company. They stack, and each one lays the groundwork for the next.
Key points:
Visibility and alignment come first, because without visibility you cannot align, and without alignment you head north while your partner heads east
Accountability and support come next: a faster business makes more mistakes, and that is fine as long as failures are surfaced, supported, and not repeated
Enable and then empower, in that order. Empowered decision-making without enablement just distributes decisions to people who lack the frameworks to make them
His stated philosophy across everything: figure out how to not be needed. He contrasts this with the common pattern of hoarding information precisely in order to remain necessary, which he calls a non-enduring approach to leadership
The SaaS Apocalypse, Durable Right to Win, and Terminal Value
This is the analytical heart of the episode. Vic explains why software valuations are compressing, and the answer is not the one Dave initially guesses. It is not that AI drives down labor costs and therefore changes the economics. It is that AI casts doubt on whether the company will even exist in ten years.
Key points:
For a high-growth, low-profit software company, the overwhelming majority of valuation can sit in terminal value, the year ten assumption that the business persists and grows modestly into perpetuity
If AI puts a company’s durable right to win in question, terminal value does not get marked down gradually. It can go to something near zero effectively overnight, taking most of the valuation with it
The market shifts to valuing near-term cash flow instead, which is how you get from ten times revenue to something below five, and from 25x EBITDA to under 10x
Vic thinks the effect is more pronounced in private equity markets than public ones, and does not believe we are at the bottom yet
Moats increasingly live in data, but data without context is useless, so there is now a real fight over who owns the context layer
Dave’s read that systems of record hold up better than point solutions gets a qualified yes, with the observation that security is simultaneously the most entrenched category and the one Vic worries about most
What Engineering Leaders Should Actually Take From This
Dave asks what a director of engineering should understand about this economic theory. Vic’s answer is refreshingly blunt: probably not much of it, day to day. The thing that matters is accepting that the way knowledge work happens has changed, and that embracing it is not optional.
Key points:
The internet and mobile are the reference cases. Organizations that did not embrace them are largely not around to discuss it
The difference with AI is pace and direction. Prior technologies expanded opportunities for knowledge workers; this one can displace them
Embracing it doesn't make your existing job slightly easier. It is re-architecting the job from scratch in the context of the new technology, function by function
Not everyone will make that transition, and Vic says plainly that this is going to be okay, while the people who do will operate at a different level entirely
On Jevons paradox and new job categories, Vic expects yes eventually, but flags the transition problem: if AI removes early career roles, the grooming path to senior roles disappears with them
His proposed answer is education and a redefined entry level. At Tempo, entry-level means new builders, as in building agents and agentic flows
Why Legacy PPM Failed, and What Puts the S in SPM
Vic’s time at Planview showed him both the promise of strategic portfolio management and exactly why the traditional approach frustrated customers. The problem was the delivery model as much as the software: one giant codebase, one giant implementation, and a requirement that the whole company change how it works.
Key points:
Product and engineering have always been the darkest spot in a CFO’s view of the business. Hours worked and lines of code tell you nothing on their own; the value is in connecting the dots
The monolithic implementation model produced a vicious cycle where customers were always partly unhappy, which made growth, customer satisfaction, and employee satisfaction all harder
Tempo’s counter approach breaks SPM capabilities into individually consumable applications, with time to value measured in days or weeks and often no human touch to get started
Small surface areas mean rewriting or augmenting a component is not a big deal, which Dave flags as a nice illustration of architecture functioning as a strategic capability rather than a cost center
On the S in SPM: what SPM supports is the company’s core strategy, because for most companies strategy is expressed as products and services, and delivery of those is the lifeblood
Vic ties this directly back to his valuation argument, arguing a company’s sustaining durable right to win is bounded in what it builds and ships
The Bottleneck Moved, and Now It Is Everywhere
Dave describes grabbing a hunk of slime: squeeze the delivery bottleneck, and it squirts out either side. Vic agrees and describes customers dealing with the consequences upstream in planning and downstream in commercialization, support, and feedback loops.
Key points:
Annual product planning is finished. Quarterly is the floor, and it has to reach the highest level of strategy, not just the roadmap
Most companies are in a hybrid state right now, still partly constrained on delivery while starting to feel the new constraints
As soon as you release one limiter, you find all the others, and SPM touches most of them: what to build, how to commercialize, how to implement, how to service, how to route feedback back to product
Team shapes are changing in response to what agents are good at. Vic describes going from eight-person teams to teams of two or three for some work and six for others, with the mix expected to keep shifting
With throughput up several fold and cycles down to weeks, managing the portfolio the old way is, in his words, literally impossible
Attribution becomes the new measurement discipline: understanding the economic value of a person versus an agent versus both, and being able to show the organization why those calls were right
Vic is candid that the hardest part of this for leadership is the scenarios where the answer for a given person is no
Org Design as a Revolution, Not an Evolution
Dave raises something he says he has almost never seen done well: a continuous, data-informed org design capability, rather than a big transformation every three years when leadership turns over. Vic says it is not a problem Tempo solves, but it is very much one he is wrestling with.
Key points:
Vic is a believer in evolution over revolution as a general axiom, and says flatly that this is no longer the case. Right now, it is a revolution
The traditional model distributed distinct skill sets across layers and functions. Agents now have many of those skills, which breaks the model rather than adjusting it
His current working construct is four categories of work: architecture, orchestration, builder, and field operations
Builder is the one he considers most important right now, spanning every function, and field operations cover everything an agent-first approach still requires people for
He describes having to push some of the smartest people at Tempo over the hump of actually building agentically, and compares the moment it clicks to a first scuba dive, where you knew there was something under the water but could not appreciate it until you were in it
The Orchestration Problem
Dave’s own episode notes had AI inside the product, and the orchestration problem it creates as a topic, and Vic takes it in three parts: knowing what to work on, deciding where to deploy resources, and then managing the human consequences of a system that can replan continuously.
Key points:
Tempo is preparing to introduce a market and competition module on its AI native platform, on the premise that competitive signals now need to feed roadmap decisions in something close to real time
Resource deployment follows: reading signals about what is behind, ahead, or worth canceling, then orchestrating people and agents against that
The subtle problem is change management. A fully automated system that constantly re-optimizes will tell a developer to switch tasks every five minutes, which is unworkable
The fix is automating change management alongside the replanning, so shifts arrive with a rationale and within sensible time parameters
His analogy for scale: he still runs a mid-sized business, but the throughput means he is now managing traffic for a city rather than a town
Dave connects this back to Nerd/Noir’s framing that flow matters, but outcomes matter more, and that leaders should incentivize insight and roadmap adjustments rather than raw shipping. Vic’s response is that outcomes are what let flow keep flowing
Culture, Remote First, and Employee Engagement as the Metric
The episode closes with Vic running a remote-first company, which turns out to be the axioms again, plus radical transparency about how decisions are made and who makes them.
Key points:
Transparency means everyone understanding what decisions were made, why, who made them, and how to provide input, precisely because Vic assumes he is not the best person to make most of them
Scalability principles give the organization a shared way to decide: simplify, standardize, and consider the customer experience and sustainability. Tradeoffs are expected, but decisions aligned to those four are probably good ones
What he hires for on a leadership team: some been there done that so the group is not experimenting on every front at once, strong people orientation, and a real appetite for experimenting and therefore for failing
The test he applies is whether he can be absent from the room and still be confident that the decision his CRO, CPO, or CTO makes is the right one
Employee engagement is his candidate for the single most important metric at a software company, on the argument that employees ideate, build, sell, and support everything the company does
It is also one of the rare metrics with a genuinely bidirectional win. You spend roughly half your waking hours at work, so engagement bleeds into life outside it in both directions
On making principles stick: out of sight, out of mind, so treat them like a marketing campaign. Regular repetition for adoption, semi-regular for maintenance, drip feed rather than ten frameworks at once, and above all make it visceral with examples
Hard Boiled Software is hosted by Dave Laribee
