A case for promoting Tom Dehmer to Sr. Director, Global Solution Engineering
You are absorbing Dave Simon's sudden transition to GM of Americas while simultaneously navigating one of the most significant Customer Outcomes restructurings this company has seen. The SE org is ready for change, and needs a fully focused leader who can move now. In addition, this move likely saves Ironclad in excess of $150K in year one alone against market VP rates, and we could bank every penny if needed. But a portion could also be deployed to shore up key players throughout the organization. You get the right Solutions leader in place to move fast, you shore up the most important players in the SE org, and you still come away with savings for the company. This is not just a win-win, it's one plus one equals three. The leader we need is already here. Let's Make It Happen.
Jim Farley has been a good leader to this team, and that matters. But being well-led is not the same as being Solutions-led. The SE org now faces the demands of a modern, AI-first sales environment, and it needs a dedicated leader who lives and breathes the pre-sales motion. Decoupling from the Customer Outcomes structure was a necessary first step, removing the natural friction between a post-sales org and a team of technical sellers. But it is not enough on its own. Jim's focus has formally shifted to the Forward-Deployed Architects and Enterprise Architects, the work where his skills and background are strongest, and that is exactly the right move. What it creates is a clear opening: a chance to bring in Solutions-first leadership at the moment the team needs it most. The Pulse survey confirms the urgency. "Fit and belonging" scores dropped to 50 for new members. DEIB, while 86 overall, also sat at 50 for new hires. The team is ready for direction. The window to act is now.
Tom is beyond 100% on the Sr. Mgr pay scale and carrying Director-level scope without the title: field messaging, cross-functional initiatives, org-wide training, global onboarding, sales and trial process improvement, and day-to-day partnerships with PMM, Product, CO, and our Partners. He manages 9 SEs directly, from Sydney to Rio, touching every US timezone. The title is the only thing lagging. Correcting it is structural accuracy, not a stretch.
Tom is actively applying for the VP of SETS role and, after conversations with many levels of leadership throughout the company, should be a leading candidate. In that context, Sr. Director is the calibrated, conservative step. If Tom is right for the VP role, this confirms it. If not, the org has a capable Sr. Director who knows the team and the product. Either way, Ironclad wins.
Tom is promoted to Sr. Director, reporting directly to you, with full ownership of the global SE org. Marisa Bloodgood's Demo Engineering and RFP Analyst teams move under Tom's org as well. Tyler Andersen's Director promotion follows in the mid-year cycle, mitigating the potential for his attrition. Jim Farley focuses fully on FDE and EAs. One backfill headcount opens, with strong internal and external candidates already identified.
Tom temporarily continues to support emerging markets accounts directly during the transition.
The alternative to this promotion is an external search for a VP of SETS. Market rates for that role at growth-stage SaaS companies run $450–500K+ OTE, plus an executive search fee of $70–100K. That, plus a 6 month+ ramp before the org has a grounded, trusted, functional leader. Even if Tom is the eventual hire, the process alone costs 2 to 3 months. Tom is internal and asking to come in as Sr. Director, both of which significantly lower his cost profile. The delta between those two scenarios is well in excess of $150K in year one alone, before equity. We pocket a solid chunk of that savings, but let's also use it as capital to stabilize a strong team which is ready to accelerate. Josh Eich's departure as SVP of Enterprise Sales makes this move even more critical.
Like Tom, Tyler is operating above his payband. Nominations open in two weeks. If he is not promoted in this cycle, the retention risk becomes real. Correcting comp alongside the Director title is the right move now.
"Fit and belonging" dropped to 50 for new members. DEIB overall was 86, but also 50 for new members. A mid-Q3 tech summit addresses this directly. Budget is less than $60K, partially offset by redeploying Australia training funds to bring Paul Guerin to the US for this training. Tom delivers a full business case within one week of the org change, but a focus on Procurement, AI enablement, and aggressive selling moves the org forward and stabilizes the team as a whole.
Phase 1 is immediate. Tom can start tomorrow. Everything below is conditioned on growth and performance, not a commitment.
Tom takes ownership immediately. The org chart above is the new structure. Top internal candidates for the backfill include Zach Reed, Ernesto Carrera, and Angela Everard. Promoting one takes care of another top performer's career path. External options are available if needed.
Tyler is promoted to Director with compensation corrected to match. As soon as appropriate, he moves to second line, still reporting to Tom. Work also begins on defining the Distinguished SE role, which offers a career path to the very best of our individual contributors.
Tyler takes on Midmarket and CAE managers as direct reports. LAIS continues to report to Tyler. Six months behind, Caitlin Chenier is promoted to Director, taking over Tyler's Enterprise team. Backfill to Tyler's second-line move is likely sourced externally. Tom operates as a 2.5-line manager. Org cost still sits below what a single external VP hire would have cost, with the top leaders retained and promoted from within.
The current need is a growth-ready second line, which Tom can absolutely fill and grow into a third-line role as the business genuinely requires it. Assuming growth trajectory holds and Tom is performing, Tom moves to VP. Caitlin, Negin, and possibly Mel move into second-line roles, backfills sourced externally. A Distinguished SE role reporting directly to Tom is created, with Bud Esquibel as the most likely candidate. None of this is automatic. It is a plan, not a promise.
| Objection | Response |
|---|---|
| "Is Sr. Director too big a jump?" | Tom is already beyond 100% on the Sr. Mgr pay scale, managing 9 SEs across a near-global footprint from Sydney to Rio, leading field messaging, cross-functional initiatives, and day-to-day partnerships with PMM, Product, CO, and our Partners. He is carrying Director-level scope today. The jump is in title, not in operating reality. |
| "What if Tom is not performing by EOY FY27?" | The roadmap is conditioned on performance and growth. If Tom is not meeting expected progress and milestones, an outside third line is brought in when expansion has truly required it. Accountability is built in. |
| "What does this do to Jim Farley?" | Jim has been splitting focus between interim SE leadership and two technical teams waiting for his full attention. This change is a relief, which gives Jim the space to move his org forward immediately. |
Approve Tom Dehmer to Sr. Director, Global Solution Engineering. Commit to Tyler Andersen's Director promotion in the mid-year cycle. Open the backfill headcount. Shore up the top ICs in the SE org. Confirm budget for the Q3 SE onsite training. Free Jim Farley to focus fully on the Forward-Deployed Architects and Enterprise Architects.
The solution is already in the building. Let Tom take the SEs off your plate, save the company in excess of $150K in year one alone versus an external VP search, and get the transformation to an AI-forward Solution Engineering team underway. If we are going to hit our sales targets, we need a focused, energized SE team pushing hard on the future of our solution. We cannot wait another day, let alone another quarter.