Executive Search for the Leaders Who Own Your Enterprise Systems

The VP who built your business systems team gives notice, and nobody internal is ready to step into the seat. A CIO retires after fifteen years and the institutional knowledge walks out the door with them. A new ERP or CRM program gets board approval and there’s no one on staff who has run something that size before. Private equity closes and the sponsor wants a systems leader who has been through an integration. The last person you hired into this role didn’t work out, and you can’t afford a second miss.

These are the moments that bring companies to an executive search, and none of them arrive at a convenient time.

Oakcrest runs executive search for enterprise application leadership at mid-market companies. Chief Information Officers, VPs of Enterprise Applications and Business Systems, IT and Digital leaders, and the practice leaders who run delivery organizations at consulting firms and system integrators. We work across the platforms these leaders own, including Salesforce, NetSuite, Workday, and the integration layer that holds them together.

why mid-market executive search is its own problem

The large retained firms are built for public company C-suite work. A VP of Enterprise Applications role at a $400 million manufacturer doesn’t get their senior attention, and the fee structure rarely makes sense on either side. The contingency market has the opposite problem. You get resumes on day two, most of them active job seekers, and no real assessment behind any of them.

What’s missing in the middle is a search that is actually run. A defined role, a mapped market, direct outreach to leaders who aren’t looking, honest assessment, and a short slate you can act on. That’s the work we do.

when executive search is the right model

Not every leadership opening needs a retained search. These are the situations where it consistently pays for itself.

  • The role is critical and the market is small. There are only so many people who have modernized a mid-market ERP and CRM stack and lived with the results. They are almost all employed. Finding them takes deliberate market mapping, not a job posting.
  • The search needs to stay confidential. You’re replacing someone who is still in the seat, or the news would unsettle a team, a customer, or a lender. A retained search keeps the process contained and gives you a single point of contact who understands what’s at stake.
  • The last hire in this seat didn’t work. Something in the definition of the role, the assessment, or the expectations was off. Before we work the market, we want to understand what happened, because repeating the same search usually produces the same result.
  • The role is new to your organization. First CIO. First VP of Business Systems. First real owner of enterprise applications. When there’s no precedent internally, defining the role correctly matters more than sourcing speed.
  • A transformation is funded and the clock is running. Board approval, an acquisition to integrate, a platform decision already made. The cost of leaving the seat empty is measured in program delay, not in salary.

what we assess that a resume won’t show

At this level, everyone we talk to has run a large program on paper. The difference between candidates shows up in four places, and you only learn to spot them by working next to a lot of people who held these jobs.

  • Whether they led the transformation or were present for it. Plenty of executives have a major implementation on the resume. Fewer made the hard calls, owned the scope fights, and were still there when the organization had to live with the design. We ask questions that separate the two.
  • Whether they can hold a room with the CFO and the architect. The leaders who succeed in these roles translate in both directions. They can defend a capital request in business terms and challenge a technical design without losing the team’s respect. We’ve watched leaders do that well, and we’ve watched others lose one room while trying to win the other. It’s a rare combination, and it shows up quickly in a conversation.
  • Their judgment about AI and automation. Every executive says the right things about AI right now. The useful question is whether they can tell a real capability from a vendor demo, and whether they know what has to be true about your data and processes before any of it works. Enthusiasm is common. Discernment isn’t.
  • How they build and keep a team. A leader who can’t attract talent becomes the bottleneck in eighteen months. We look at who followed them, who they developed, and who still takes their call.

how our executive search works

Executive searches are run on a retained or engaged basis, with fees staged across the search rather than paid on placement. That structure exists for a reason. It buys you dedicated effort, a mapped market, and a search partner who is accountable for finishing, not just for being first with a resume.

  • We define the role before we work the market.

    We spend real time on your current state, what this leader has to accomplish in the first year, who they’ll need to influence, and what went wrong last time if there was a last time. Most job descriptions are written to attract candidates. We write our own understanding of the role so we can evaluate against what the job actually requires.

  • We map the market rather than post it.

    We identify the companies where this experience exists, build a target list of leaders, and go to them directly. The strongest candidates for these roles are employed, delivering, and reasonably content until the right conversation reaches them. Twenty years of relationships in this space is what makes that conversation possible.

  • We assess before we present.

    Every candidate we bring you has been through a substantive conversation about their actual delivery record, not a screen against a keyword list. You get a short slate with a written point of view on each person, including where we have reservations.

  • We stay in it through the offer and the start.

    Executive offers fall apart over things nobody discussed early enough. Compensation structure, reporting lines, counteroffers, family logistics. We work those issues in the open long before an offer letter goes out, and we stay involved through the first ninety days.

confidential searches

A meaningful share of executive searches can’t be announced. The incumbent is still in the seat, or a public search would send the wrong signal to a customer, an investor, or a team already feeling uncertain. We run these searches without your name in the market until a candidate is qualified and you’ve agreed to disclose it. You get one point of contact, no coordination across a bench of recruiters, and no posting anywhere.

LEADERSHIP ROLES WE PLACE

Our searches focus on the layer where technology decisions and business outcomes meet.

  • Chief Information Officer and Chief Technology Officer
  • Chief Digital Officer and VP of Digital Transformation
  • VP and Director of Enterprise Applications
  • VP and Director of Business Systems
  • VP of Information Technology
  • Chief Enterprise Architect
  • VP of Data and Analytics
  • VP of Revenue Operations, where the CRM and quoting stack reports
  • Practice Directors, VPs of Consulting, and Delivery Leaders at system integrators and consulting firms

why organizations trust oakcrest

Most search firms learn about enterprise systems by talking to the people who run them. We spent twenty years working alongside them. Our founder spent nine years at Salesforce in engagement leadership and twenty years delivering and leading enterprise implementations, which meant sitting across the table from CIOs and VPs of Business Systems at company after company, running programs with them and seeing how each one handled the parts that don’t appear in a status report. Some of those programs landed. Some didn’t. The difference was rarely the technology.

That’s the pattern we bring into an executive search. We know what the leader in this seat does when the integration slips, when the CFO wants the number cut in half, and when the team needs someone to absorb pressure instead of passing it down. It shapes the questions we ask and, more importantly, what we listen for in the answers.

That background changes the conversation on your side too. We’ll tell you when a set of requirements describes two different people. We’ll tell you when the compensation you’ve budgeted won’t reach the market you’re targeting. We’ll tell you when we’re not the right firm for a search. An honest read early is worth more than an agreeable one.

Oakcrest Talent Partners is a member of the Dimensional Search® network, an established group of independently owned executive search firms.

for executives considering a move

If you’re a CIO, VP, or senior enterprise applications leader thinking about what comes next, whether that’s this quarter or eventually, we’re worth a conversation.

We work with mid-market companies that understand what this layer of leadership is worth, and much of what we place never reaches a job board.

ready to discuss the role?

Does any of the above sound like where you are right now? Tell us about the position, the timeline, and what this leader needs to accomplish. We’ll give you a straightforward read on the candidate market, what similar searches are taking, and whether this is a search we can run well for you.