Firsts and exits: women at the top this month

At a glance: In early October 2026, Highmark Health named president Karen Hanlon its first woman CEO, effective 1 January 2027, and the World Trade Centers Association named Annette Gregg its first woman CEO in 57 years, effective 5 October. At General Dynamics, Phebe Novakovic, CEO since 2013, will hand over to Danny Deep on 1 January 2027 and become executive chairman. Hanlon's rise through an internal president role reflects a common route to the top.

Karen Hanlon: the internal track

Highmark Health announced on 6 October that its board had appointed Karen Hanlon as chief executive and president from 1 January 2027. She is the first woman to lead the Pittsburgh-based health and insurance group as CEO. David Holmberg, chief executive since 2014, will become executive chairman.

Hanlon's career is a textbook internal ascent. She started in public accounting at KPMG and joined Highmark in 1997. She held finance leadership roles, became chief financial officer in 2014, chief operating officer in 2018 and president in 2025. Along the way she led the group's affiliations with health plans in five more states, including Health Now in New York and Blue KC in Kansas City, oversaw the acquisition of Gateway Health, now Highmark Wholecare, which added Medicaid products, and led Allegheny Health Network's first $1 billion tax-exempt bond financing.

Her stated priority is "making healthcare more affordable, simpler, and more effective for the people and communities we serve." Board chair Greg Jordan said: "The Board has tremendous confidence in Karen's ability to lead the organization into its next chapter."

The organisation she will run has grown from about $17 billion of revenue in 2014 to a projected figure close to $35 billion by the end of this year, according to Highmark.

Annette Gregg: the outside hire

The World Trade Centers Association took a different route. On 5 October it announced Annette Gregg as chief executive with immediate effect, the first woman to hold the role in the association's 57-year history. The WTCA links more than 300 World Trade Center locations across nearly 100 countries and territories, and its global headquarters is at One World Trade Center in New York.

Gregg came from outside. She was most recently chief executive of the Society for Incentive Travel Excellence (SITE), a global association of about 3,700 members and 27 chapters, where the WTCA says she delivered a 160% rise in topline revenue over three years and membership growth of more than 70%. Before that she was chief revenue officer at Meeting Professionals International, responsible for about 70% of its revenue. She has more than 30 years of experience across global associations, private enterprise and international business events.

John E. Drew, chair of the WTCA board, said Gregg "brings the combination of strategic vision, financial acumen and global stakeholder engagement that WTCA needs." Gregg said: "I'm honored to lead WTCA into this next chapter."

Phebe Novakovic: a planned exit

At General Dynamics, the news ran the other way. On 7 October the board elected Danny Deep, the company's president, as chief executive from 1 January 2027. Phebe Novakovic, CEO since January 2013, becomes executive chairman.

Novakovic took over as the defence market moved into sequestration and lower military demand, and built a reputation for disciplined operations and cash management. Under her leadership the company made its largest acquisition, buying CSRA for $9.7 billion in 2018. General Dynamics reported $52.6 billion of revenue in 2025 and employs more than 120,000 people.

WCRC analysis: Her move to executive chairman means one of the most prominent women in the global defence industry will remain in the boardroom, but the number of women running major defence contractors day to day becomes smaller. Her successor, like Hanlon, comes through a president role.

Why so many firsts come through the president's office

WCRC analysis: Hanlon's path, finance to COO to president to CEO, is one boards find easy to trust. The president or COO role lets a board watch a candidate run the whole business before handing over the title. Three of this month's large-company successions, at Highmark, General Dynamics and Stryker, were filled by serving presidents.

For women, that route has advantages and limits. The advantage is that it rewards long, visible performance inside one organisation, where results speak louder than networks. Hanlon spent 28 years at Highmark before her appointment. The limit is time. A track that requires decades in one company, and a sitting CEO willing to create a president role, moves slowly. Where boards do not create that stepping stone, internal women candidates may never get the chance to be tested at the top.

Gregg's appointment shows the other path. Membership bodies and associations often hire chief executives from peer organisations, valuing a record of growing revenue and membership elsewhere. Her SITE results were central to how the WTCA presented its choice.

What the month tells us

WCRC analysis: A handful of appointments does not make a trend, and the number of women leading large organisations remains small. But the month shows two practical things. Firsts are still being recorded in organisations that are decades old. And the clearest route to the top, for women as for men, still runs through a role in which the board can see a candidate run the business before it decides.

What it means for leaders

• If you want a diverse CEO shortlist, create the proving-ground roles early: president, COO, or a large business unit with full P&L.
• Rotate high-potential leaders through finance, operations and strategy; Hanlon's CFO-COO-president path is a strong template.
• Do not rely only on internal tracks. External hires, as at the WTCA, can bring proven growth records from comparable organisations.
• Plan for the continuity role of departing leaders, so a successor's authority is clear from day one.

Quick answers

Q: Who is Highmark Health's first woman CEO? A: Karen Hanlon, currently president, becomes CEO and president of Highmark Health on 1 January 2027, the first woman to hold the CEO role.

Q: Who is the new CEO of the World Trade Centers Association? A: Annette Gregg, formerly CEO of the Society for Incentive Travel Excellence, became WTCA chief executive on 5 October 2026, the first woman in the role in its 57-year history.

Q: Is Phebe Novakovic leaving General Dynamics? A: She steps down as CEO on 1 January 2027 and becomes executive chairman. Danny Deep, the company's president, succeeds her as CEO.