Talent Decisions for Portfolio Company Leadership
Last week, we explored how countless portfolio companies find themselves like Beckett's characters in “Waiting for Godot,” postponing AI adoption while competitors build insurmountable advantages. The same paralysis affects critical talent decisions. While some firms wait for the "perfect" AI-ready candidate to materialize, others are actively building the AI-enabled leadership teams that will define tomorrow's competitive landscape.
As portfolio companies navigate an increasingly AI-driven business environment, talent decisions have become exponentially more complex. The question isn't just about finding the right person for the job, it's about finding someone who can leverage AI to transform how that job gets done.
The Talent Waiting Room
Just as companies convince themselves that tomorrow will bring the perfect moment to implement AI, many fall into similar thinking around leadership hiring:
"We'll find an AI-savvy CFO when the market settles."
"Let's wait until AI skills become more standardized in marketing."
"We need to see how AI impacts operations before we hire."
This hesitation creates the same costly delays we discussed last week. While you debate the perfect hire, competitors are building AI-literate leadership teams that are already driving measurable results.
A Critical Hiring Scenario
Consider a situation facing a new portfolio company of a middle market PE firm. They need to fill three key positions—CFO, CMO, and VP of Logistics. They have five strategic approaches:
Hire from within - promote existing talent without additional AI investment
Hire from within and provide AI upskilling - internal promotion with structured AI capability development
Hire from outside - external recruitment focused on traditional competencies
Hire from outside with AI screening - external recruitment prioritizing existing AI fluency
Hire from outside and provide AI upskilling - external recruitment with structured AI capability development
Each path carries advantages, risks, and implications for your company's competitive trajectory.
Finding Your Next CFO
When a qualified internal candidate is ready for a C-suite position, they often present a superior choice over an external hire. Their existing knowledge of the company's operations and history allows them to integrate seamlessly, with their learning curve focused on essential AI upskilling. This is particularly crucial for roles like CFO, where AI-first leaders can revolutionize financial planning, risk assessment, and investor relations through advanced predictive modeling and automated reporting.
If no internal candidate is suitable, an external search becomes necessary. Beyond relevant industry experience, prioritize candidates with proven AI experience in their previous roles. Screening for "AI-first" talent signals innovation readiness to stakeholders and delivers immediate operational benefits, including sophisticated scenario planning, enhanced risk modeling, and accelerated financial reporting cycles.
Should your external search fail to identify a qualified candidate with existing AI experience, assess top candidates' interest in AI upskilling. Integrating a desire to leverage new technologies into your screening process is increasingly important for leadership roles. Candidates with a growth mindset will be attracted to the opportunity that you will provide them AI tools and training.
Finding Your Next CMO
Marketing is being fundamentally transformed by AI. Customer segmentation, content personalization, attribution modeling, and campaign optimization now require sophisticated AI fluency to compete effectively and manage to budget. If your marketing team is not AI-enabled, you may prefer to recruit an AI-first CMO from the outside. Depending on your budget and industry, however, finding that unicorn candidate may be difficult.
If your marketing team is at least experimenting with AI, the perfect candidate ready to learn more may be on your payroll and can hit the ground running with institutional knowledge. Provide the whole marketing team functionally-specific AI training, encourage testing of marketing use cases that accelerate output, empower more content personalization, and bring production efficiencies in-house.
If you must search for an external candidate and can’t find that unicorn candidate who can bring an experienced AI-first approach, then screen for a growth mindset. If a candidate isn’t excited by the opportunity to access AI tools and training to transform your marketing plan, they will slow you down and always be asking for more budget to do less than your AI-enabled competition.
Finding Your Next VP of Logistics
Internal promotion with AI upskilling is strongly preferred in operations because logistics success depends heavily on institutional knowledge, which ties into understanding your specific supply chain, vendor relationships, and operational quirks. Adding AI capabilities to this foundation creates the most potent combination.
Internal candidates understand existing systems and relationships. Armed with institutional knowledge and AI, they are best positioned to initiate supply chain optimization, predictive maintenance, and demand forecasting, which can result in significant ROI. External hires may disrupt established vendor relationships while learning the ropes and may encounter more resistance from staff wary of outsiders with new ideas.
If your company lacks modern reporting capabilities and has broken logistics operations, then fresh expertise with an AI-first mentality may outweigh institutional knowledge. Then, hiring an AI-first logistics expert can be your best prescription to professionalize your operations.
Your Strategic Reality
In today’s business environment, the question isn’t whether to prioritize AI capabilities; it’s how to balance AI fluency with role-specific expertise and cultural fit. The winning formula may vary by function, but one constant emerges: ignoring AI capabilities in hiring decisions increasingly represents a strategic blind spot that competitors will exploit. The companies that master this balance—building AI capabilities internally and screening for an AI-first growth mindset externally—will create competitive advantages.
The Urgency of Action
Unlike Beckett's characters who remain paralyzed by anticipation, successful PE firms must make decisive talent moves today. Organizations that invest in comprehensive AI training for their teams will have more strategic hiring flexibility and a built-in talent advantage that compounds over time. When your workforce is already AI-fluent, you can promote from within with confidence rather than competing for scarce external AI talent.
If you would like to learn more about developing practical talent strategies and AI adoption plans for your portfolio companies, NextAccess can help. Contact us to schedule a complimentary consultation.
NextAccess Authors: Scott Kosch and Valerie VanDerzee
NextAccess guides organizations through AI transformation by fostering sustainable change that optimizes operational excellence while ensuring individuals are engaged, upskilled, and empowered to flourish. We specialize in helping our clients achieve breakthrough improvements in productivity, efficiency, and quality by unlocking the full potential of their people and capabilities.
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Message Scott Kosch or Valerie VanDerzee to schedule a complimentary 30-minute consultation to explore how our expertise can help your organization.