Jennifer Ingraffea is a seasoned executive leader with over 25 years of experience in the retail, apparel, product merchandising, and management sectors. In July 2025, Jennifer became the CEO of Pendleton Woolen Mills; a family-owned business since its founding in the 1860s. Before joining Pendleton, she served as Chief Product & Merchandising Officer at The North Face, prior to which, she worked at Nike in a number of high-level executive leadership roles. Jennifer and Roy discuss her new role and dig into essential leadership skills like curiosity, stewardship, and much more.

Highlights from our conversation include:

• Core beliefs, values, and principles in Jenn’s leadership playbook (2:53)
• Leading through cycles of massive consumer and retail evolution (5:39)
• Identifying areas of a business that are in need of clarification and simplification (7:36)
• Aligning a team towards a long term vision (11:01)
• Lessons learned around hiring and team building at major brands (14:58)
• How Jenn developed her hiring process and philosophy (17:07)
• What a great leader looks like to Jenn (18:36)
• Valuable traits that Jenn identifies when hiring direct reports (22:58)

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Kiernan Laughlin is the General Manager and co-creator of Deep Indian Kitchen, a growing CPG brand whose mission is to bring a modern, high-quality Indian food experience to consumers worldwide. Kiernan previously held senior brand management roles at large CPG companies like Johnson & Johnson and Unilever, and he spent his early career in marketing, promotions, and partnership leadership at Gorton’s Seafood.

Highlights from our conversation include:

• Core business and leadership lessons from Kiernan’s career in multi-stage CPG (1:26)
• Useful skills Kiernan picked up outside of work that have percolated into his leadership style (5:27)
• Going from a structured corporate environment to leading an emerging brand (8:01)
• The challenges and opportunities of building a team through rebranding (11:22)
• Elements that make a successful relationship between CEO and Founder (19:36)
• Keeping his team aligned and agile as the company evolves (21:48)
• Hiring for qualities that go beyond the resume (22:49)
• How Deep connects their mission to action through their foundation (27:08)
• Advice for the next generation of CPG leaders (30:13)

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Executive leader and board member Wilma Wallace joins Roy to discuss her experience recruiting and mentoring leadership teams at Gap and REI during her extensive career at both legacy brands. After spending over 20 years in senior roles at Gap, Wilma served as Chief Diversity and Social Impact Officer, as well as Chief Legal Officer at REI. In 2024, she retired to focus on impacting change, particularly from an equity, access, and justice perspective, on several boards. Her work centers social impact, environmental justice, and human rights in both the for-profit and non-profit sectors. Wilma and Roy discuss accounting for and addressing changing levels of trust across organizations, internal succession planning versus seeking external candidates, the link between alignment of purpose and successful performance in leadership teams, and much more.     

Highlights from our conversation include:

• How Wilma evaluates candidates’ leadership abilities (4:18)
• Creating an environment that fosters high potential future leaders (6:48)
• Recruiting external talent (8:26)
• Leadership assessment practices at Gap & REI (11:08)
• Ensuring that an organization’s culture stays dynamic and resilient (14:01)
• Leading and hiring through periods of growth and change (17:35)
• Ways in which leaders should be vetting culture and values before taking on new leadership roles (20:30)
• What gives Wilma hope about the next generation of leaders (23:00)

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Talent acquisition expert Heather Flynn joins Roy to discuss the ins and outs of successful recruitment strategy. Heather recently served as the SVP of Talent Acquisition for Aritzia, prior to which she led hiring efforts for other major brands like Nike and ASML. Roy and Heather dig into the essential role of talent strategy, the importance of strong employment branding and candidate engagement, the emerging application of AI in recruiting, and much more.

Highlights from our conversation include:

• How holistic talent strategy informs a successful business strategy (5:52)
• Current trends, challenges, and opportunities facing top talent acquisition leaders (7:54)
• Key elements of a successful talent acquisition strategy (9:58)
• How Heather assesses an organization’s hiring bar (13:45)
• Ways that hiring leaders can step up their game (16:11)
• Heather’s approach to helping hiring teams make the best candidate decisions (17:45)
• What growing consumer brands look for in a leader and how it’s evolved recently (20:07)
• How she approached talent strategy at Aritzia (22:14)

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Coach, speaker, and author Patrick Galvin joins Roy to discuss the principles laid out in his recent book The Connector’s Way. Patrick’s work focuses on the essential role of personal connection and relationship building in our day to day life, our business practices, our sense of success, and more. As co-founder and partner of The Galvanizing Group and author of several books exploring the nuances of social connection and trust building, Patrick helps high-performing companies and individuals achieve greater levels of success in business by strengthening internal and external relationships. Patrick and Roy dig into the many ways to practice relationship building, the pitfalls of networking without connecting, why it pays to be “the keener,” and much more.

Highlights from our conversation include:

• The important distinction between connecting and networking (5:02)
• Ways in which hybrid/remote work impact connection (7:11)
• Using Patrick’s methods to build trust, engagement, and performance (9:16)
• Embedding relationship building into company culture and leadership development practices (12:53)
• The intersection of connection and recruiting (18:52)
• Balancing work, life, and maintaining strong relationships (20:58)
• Metrics that leaders can use to track or improve their ability to foster connections (26:36)
• How Patrick sees technological advances impacting the formation and maintenance of relationships (29:59)

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Fred Miller and Judith Katz of The Kaleel Jamison Consulting Group have spent the last few decades on the cutting edge of diversity and inclusion thought leadership and organizational development. For the last 50 years, KJCG has assisted organizations in creating inclusive, collaborative workplaces that leverage differences to achieve higher performance and engagement. Judith and Fred have co authored multiple books on diversity, inclusion, collaboration, trust, authenticity, and teamwork, and they join Roy to discuss their latest groundbreaking book, The Power of Agency: Cultivating Autonomy, Authority, and Leadership in Every Role.

Highlights from our conversation include:

• The next crucial step beyond inclusion and diversity (2:30)
• How agency impacts organizational efficiency and performance (4:24)
• The key difference between empowerment and agency (7:18)
• A leader’s role in an agency-forward organization (8:50)
• How to evaluate a leader for their capacity to promote agency (10:00)
• What this leadership shift means for organizations (11:10)
• How the COVID 19 pandemic influenced changes around agency (12:28)
• Six critical factors that foster a culture of agency (16:00)
• How to avoid a “runaway train” when implementing this strategy (18:36)
• The first steps leaders can take toward unleashing agency (20:42)
• How to evaluate the level of agency in an organization (22:45)
• Common barriers in unleashing agency (23:30)
• The important distinction between being kind and being nice (24:55)
• How AI and other technologies might affect agency in the workplace (27:06)

Visit HowIHire.com for transcripts and more on this episode, and check out Roy’s past conversation with Fred and Judith on recruiting, supporting, and retaining a diverse workforce.

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Career coach and HR consultant Kate Sargent returns for the third installment of our series exploring tips, insights, and advice for job seekers. Kate is the founder of KJS Consulting, where she helps candidates prepare and polish all aspects of their job search strategy. Prior to starting her coaching business, she recruited for brands like The North Face, Allbirds, Method, and The Citizenry. In Part 3 of their deep dive, Kate and Roy discuss the art – and science – of negotiation. Together, they dig into the complexities of reaching agreeable compensation for a new role, the pros and cons of equity, how to leave a job graciously, and the importance of maintaining positivity through employment changes. 

Highlights from our conversation include:

• Negotiating compensation when fielding a job offer (1:43)
• Skillfully navigating and understanding equity, bonuses, and benefits (5:03)
• Other important variables to be aware of while negotiating a new role (7:16)
• How to quit and gracefully negotiate your exit (12:33)
• When, why, and where to get HR involved (14:27)
• The nuances of separation agreements (16:36)
• Contracting after leaving your role versus making a clean break (21:48)
• Dos and don’ts of posting on social media after leaving your job (23:02)

Visit HowIHire.com for transcripts and more on this episode, and check out Part 1 and Part 2 of Roy and Kate’s job search series, as well as our in-depth conversations about networking and interviewing.

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Career coach and HR consultant Kate Sargent is back for Part 2 of our three-part discussion series around strategies, guidance, and best practices for job seekers. Kate is the founder of KJS Consulting and has led extensive recruiting efforts for brands like The Citizenry, Method, The North Face, and Allbirds. In Part 2, Kate and Roy explore the ins and outs of interviewing. Together, they dig into important topics like recommendations for feeling and appearing prepared, ways to successfully frame competencies and experience, how to best approach challenging interview questions, and much more.   

Highlights from our conversation include:

• Important things to research about a company before your interview (1:44)
• Preparing for difficult interview questions (3:47)
• How to clearly and accurately convey leadership experience (7:14)
• Going high level in answering interview questions vs. getting into the details (9:39)
• Cues to be aware of (11:24)
• How to communicate weaknesses or limited experience (17:24)
• The value of having good questions prepared as an interviewee (20:54)
• How to follow up after an interview (24:30)

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Career coach and HR consultant Kate Sargent returns to the podcast for a special, three-part deep-dive into advice, insights, and recommendations for job seekers. Kate is the founder of KJS Consulting and has an impressive track record in recruiting for major brands like The North Face, Allbirds, Method, and The Citizenry. At KJS Consulting, Kate helps job seekers contextualize, articulate, and organize their stories in order to land ideal opportunities. In Part 1 of this conversation series, Roy and Kate dig into the functions of different kinds of recruiters, best practices for candidates in cultivating relationships with search firms and consultants, major do’s and don’ts during the hiring process, and the long range perspective necessary to building a comprehensive job search strategy.

Highlights from our conversation include:

• Ways in which Kate supports and coaches job seekers (3:12)
• Understanding the role of different recruiters and how they work (4:30)
• Why communication from recruiters might feel inconsistent or challenging at times (5:58)
• How candidates can evaluate whether or not a search firm is a good fit (10:18)
• What candidates should expect when reaching out to a recruiter (12:29)
• Effective ways for candidates to build relationships with search consultants (15:00)
• Respecting the recruiter during the hiring process (16:08)
• The importance of candidate honesty and accuracy in targeting opportunities (21:51)
• Leveraging your relationships for a long game strategy (23:43)

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Board recruiting advisor Kris Stred breaks down the role and impact of an effective board and how to find experienced directors. Kris has over 15 years of board search experience and is the founder of Stred Executive Search LLC. Before starting her own firm, Kris was a lawyer for publicly-traded and privately-held companies. Her first-hand involvement with the board’s fiduciary duties in high-stakes situations and the important dynamics of teams of business leaders propelled her to become a recruiter. She gained a deep understanding of what it takes to form a balanced and functional board of directors.

Highlights from our conversation include:

• The role and common structure of a board (3:19)
• How boards are evolving (5:59)
• When companies should develop a board (7:20)
• Why companies might look for professional support when recruiting a board (9:28)
• Pitfalls of the traditional board recruiting process and how to avoid them (11:56)
• The biggest difference between board and executive recruiting (15:27)
• What to look for in a board candidate (17:42)
• Screening for mission and values (21:14)
• One vital lesson from successes and failures (22:40)
• Mitigating risk factors (24:00)
• Key advice for incoming directors (25:27)

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