Beyond Product Management

What happens when the career you planned to stay in until retirement suddenly ends?

For Morgan Wilson, it came after ten years as a top performer in law firm and financial services recruiting. She was burnt out, had no work-life balance, and then she was laid off. She had offers to go back and do the same thing somewhere else. Instead, she took six months to figure out what she actually wanted her next chapter and her legacy to be. The Wilson Co. came out of that.

In this episode, Heather and Morgan talk about career pivots from both sides: the professional asking “Is this what I want to do for the rest of my life?” and the company trying to hire and keep the right people. Morgan explains why treating employees like a line item drives them out the door, why transferable skills often matter more than industry experience, and how AI has made job searching harder for candidates and employers alike. She also shares the human-centered matching tool she’s building to fix that.

In this episode:

• How a layoff and her lowest point became the start of The Wilson Co.
• Why you’re never fully “ready” to start, and why you have to bet on yourself anyway
• What companies still get wrong about retention (hint: it’s not another happy hour or signing bonus)
• How Morgan helps mid-career professionals map their real priorities: money, prestige, balance, or the work itself
• Why your skills carry over to other industries more easily than you think, and why an outside perspective can be an advantage
• The “unicorn candidate” problem, and what Michael Jordan’s switch to baseball teaches about hiring
• How AI-written resumes, easy-apply buttons, and keyword filters broke the hiring process
• Morgan’s AI matching tool that uses skills, goals, and video in place of resumes
• The first step to take if you have career questions you haven’t said out loud yet

Your reflection prompt:

What’s one career decision you’ve been making based on what looks good on paper? Does it actually line up with what you want for your life?

About Morgan:

Morgan Wilson is the founder and CEO of The Wilson Co., a career coaching and talent strategy firm. It works with professionals going through career transitions and with the organizations trying to hire and keep them. Before she founded the firm, Morgan spent ten years in recruiting and development at legal and financial services institutions. She’s based in New York City and grew up in Nashville.

Connect with Morgan:

• Website: wilson.co
• Instagram: @thewilson.co
• Substack: The Wilson Co.

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9

Product teams keep hearing “be more customer-centric,” but almost nobody shows them how. In this episode, Heather sits down with Jake McKee, a customer conversation strategist and longtime community builder. They talk about how product leaders, product managers and engineers can stop relying on secondhand insights and build real relationships with the customers they design for.

Jake draws on community work at Apple and LEGO, where he built the company’s relationship with its adult fan community. He has also worked with brands like Southwest, H&R Block and Canon. He explains why talking to customers isn’t the same as having a conversation with them, and why that difference decides whether you get real insight or just a polite “thanks.”

In this episode, we discuss:

• The “game of telephone” that happens when insights come secondhand from sales and support
• Why engineers who meet customers face to face build more empathy, and burn out less
• How a risk-averse business culture keeps product teams away from customers
• The difference between talking, interviewing and having a real conversation
• What to do when your user base is too big to talk to everyone, including Jake’s tiered approach of about 15 key voices at LEGO
• How to spot influential voices in your community, on your own platform, Reddit or Facebook
• Jake’s three tiers for customer conversations: introduction, curiosity, then the ask
• “Conversation debt”: what it is and how to start assessing it with your team tomorrow
• The Customer Conversation Compass: conversation debt, architecture, tuning, amplification and traction

Key takeaways:

• Conversation is a skill you can learn, just like management. Introverts can learn it too.
• Relationships are built through depth, time and repetition, not one two-hour meeting.
• Start with “What are you working on?” and let curiosity lead before you ask what you need to know.
• Your first step: sit down with your team and have a conversation about conversation. Where are you coming up short, and why?

Connect with Jake:

Jake's website

Jake's Instagram

Jake's Podcast on Spotify- The Conversation Lab

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9

It was a Thursday when the Slack message came in: “Heather, we have a problem.” In this bridge episode between product and security, Heather goes back to her corporate days in regulated health tech. Releases there had to pass gate after gate, from internal sign-offs to FDA and international approvals, and “done” and “released” were rarely the same day. She shares the day she and her release manager refused to push a release live. A run of bad releases had already worn down customer trust, and putting out another one just wasn’t safe.

Then she brings it home to small business, where you don’t have a release manager because you are the release manager. Heather walks through the four questions she asks before holding a release. What’s in it? When can it realistically go out? Do you have the capacity to test it on that date? What’s the downstream effect? She adds a bonus question about how to tell people you’re delaying. She also shares a pause from her own business. The Security Starter Kit was planned for the last day of Cybersecurity Awareness Month, but she held it a few days to re-record the videos and get it right. She’s honest that the pause still meant working in pockets of time around her family.

The episode closes with a quick security check for your own “staging environment,” like checkout pages, client portals, intake forms, and automations, before anything goes live. The big takeaway: a pause has a plan and a real date. Procrastination is just a feeling.

Mentioned in this episode

• Security Starter Kit: https://pdrmconsulting.myflodesk.com/securitystarterkit

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9

To wrap up Cybersecurity Awareness Month, Heather and John answer the question every small business owner is asking: Why should I invest in cybersecurity now?

Reported cybercrime losses hit $20.9 billion in 2025, up 26%. Agentic AI and vibe coding are reshaping the landscape fast. Small businesses don’t have the luxury of waiting. And protecting your business doesn’t have to cost an arm and a leg.

Heather also shares a story about vibe coding PDRM’s own Are You Hackable? quiz. The front end looked great, and the quiz worked. Then she and John reviewed the code from a security perspective, and they were horrified. Here’s what they found, how they fixed it, and why it matters for anyone with a quiz or lead magnet on their site.

In this episode:

• Why the cyber landscape looks completely different than it did even a year ago
• How agentic AI makes sophisticated attacks easier, and vibe coding makes vulnerable apps easier to ship
• The behind-the-scenes story of vibe coding the Are You Hackable? quiz, and the security prompts that fixed it
• Why a vulnerable quiz puts more than your website at risk: it can expose connected tools like your email platform through API keys
• John’s non-negotiables: keep API keys and secrets on the server, validate input on the server, and never trust client-side code
• What a pen test is, and why even senior developers using security tools still get one before going live
• Why 81% of small businesses reported a security or data breach last year, and how that harm compounds
• The upside: how strong security helps you win contracts and sleep better at night
• Why every business needs an incident response plan. Think fire drills and safe words for your business.

Key takeaway:

You’re building something meant to last. If you don’t protect it, it won’t. Start small with low-cost steps and better habits, and right-size your security to your business.

Resources & Links:

• Take the Are You Hackable? quiz
• Blog post on securing vibe-coded quizzes, including the prompts to use
• Join the Security Besties Community
• PDRM Consulting: pdrmconsulting.com

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9

This was supposed to be an episode about why PDRM focuses on female founders and small businesses instead of chasing big-ticket enterprise contracts. Halfway through outlining it, Heather caught herself over-explaining, and she realized why: this month she spent a lot of time on the receiving end of people explaining her own field to her.

In the final week of our Cybersecurity Awareness Month series, Heather shares what’s been happening in her comments and DMs, including men pitching their own services under her offer and giving her crypto advice when she’s never posted about crypto. She explains why it matters for every woman running a business, even if you never post about security. This isn’t a “men are the problem” episode. It’s about a pattern, and how to protect your business and your decisions from it.

In this episode, we cover:

• A critical PHP vulnerability that could affect your website, and the one message to send your web host today
• What happened when Heather offered to help founders build a security plan, and men showed up to pitch themselves instead
• Why confidence isn’t the same thing as expertise
• Three questions to ask before taking anyone’s security advice
• Why “just hire an expert” is only half the answer, and why you need to understand the ROI before signing a five-figure contract
• Why risk is personal, and why only the founder can decide how much risk the business takes on (including tradeoffs like whether contractors get a company email address)
• Why PDRM serves female founders and small businesses, and why security and business strategy belong together
• A rapid-fire recap of the whole October series

This week’s challenge: Check your website and server for the PHP update. If someone else hosts or manages your site, send them one message today: “Have we patched the PHP vulnerability?”

Resources & Links:

• Free Cybersecurity Awareness Month Training, October 28. Phishing and online safety, open to everyone.
• Security Besties. Our hands-on cybersecurity community for female entrepreneurs. Plain English, real support, no mansplaining.
• “Are You Hackable?” Self-Assessment. A free, no-pressure first step to see where you stand.
• Cybersecurity spending blog series (Parts 1 and 2). How to think about security ROI for a small business.
• Part 1
• Part 2

Something to sit with this week: Who are you letting explain your business to you? Are they helping you understand it, or just talking over you?

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9

If your idea of a phishing email is a long-lost prince promising you a fortune, it’s time for an update. In Part 2 of our Cybersecurity Awareness Month series, Heather and her husband and PDRM co-founder, John Miller, explore how AI has made phishing more realistic, more automated, and easier than ever for non-technical attackers to pull off. They also cover how AI is helping on the defense side.

In this episode:

• Why the obvious typos and awkward grammar are gone, and what AI-written phishing looks like now
• Deepfake voice and video, including the case where a finance employee joined a video call in which every other participant was a deepfake of company executives
• Agentic AI: tools that handle the research, write the lure, send it, and can even place AI-voiced phone calls automatically
• Phishing-as-a-service and MFA bypass for rent, and how they’ve lowered the bar for attackers
• Why small businesses and whole industries get targeted as the “weakest link,” plus what whaling is
• A lost-phone scam where an AI voice pretends to be an Apple Store to get your unlock code or account details
• The defense side: using Copilot or Gemini in your inbox to get a second opinion, and how AI is improving spam filters and security tools

Key takeaway: The technology has changed, but the defense hasn’t. If something feels off, it probably is. Pause, and verify through a different channel than the one that contacted you. An attacker knowing details about you doesn’t make the message legitimate.

Missed Part 1? Start with the basics of how phishing works and why you are the real target: [Part 1 link]

Resources & next steps:

• Protect the Business You’ve Built: Join our free Cybersecurity Awareness Month training on October 28. We’ll go deeper on current tools and statistics, what to look for in emails, and how to set your business up for success. Register here
• Security Besties Community: Ongoing cybersecurity support for female entrepreneurs, with standard ($100/month or yearly) and VIP ($3,000/quarter) options. Learn more

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9

Phishing is still one of the easiest ways into a business, because the attacker isn’t really after your systems. They’re after you. In the first episode of this two-part Cybersecurity Awareness Month series, Heather is joined by her husband and PDRM co-founder, John Miller. They break down what a phishing attack actually is, why every founder, entrepreneur, and team member needs to recognize one, and the simple habits that keep your business safe.

In this episode:

• Why the real goal of phishing is to steal your identity and operate inside your systems as you
• The urgency trap: how attackers count on the “hurry up and respond” mindset most of us live in
• Red flags to check: hovering over links, spoofed sender addresses, and lookalike domains (a zero swapped in for an O)
• How attackers use your LinkedIn, Facebook, and other public info to write convincing, name-dropping emails
• Common impersonation tactics: the help desk, finance, executives, vendors, and banks
• It’s not just email anymore: texts, phone calls, Slack, Teams, and multi-channel attacks designed to build false confidence
• The infamous unpaid toll text, and why the IRS and the government won’t text you demands
• Malicious QR codes, both on physical signs and inside emails that slip past filters
• The single best habit: pause, step away from your phone, and verify through a different channel

Key takeaway: Almost nothing in your inbox needs an immediate response. If a message feels urgent, that’s your cue to slow down, verify, and confirm with the sender another way before you click.

Coming up next: In Part 2, we look at how AI has changed phishing, and why today’s phishing emails look nothing like the ones you remember.

Resources & next steps:

• Protect the Business You’ve Built: Our free Cybersecurity Awareness Month training goes deeper on phishing and online safety. Register here:
• Security Besties Community: Ongoing cybersecurity support for female entrepreneurs.
• Standard membership: $100/month, with a yearly option available
• New VIP option: $3,000/quarter. It includes a one-on-one call, five hours a month of hands-on work from our team, and remediation help or additional support if something happens in your business.
• Learn more

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9

You’ve heard about the dark web a hundred times, but has anyone ever actually explained it to you? For Cybersecurity Awareness Month, Heather breaks it down in plain English, with no jargon and no scare tactics, so you know what it is, why it matters to your business, and what to do about it.

In this episode:

• What the dark web is, and why it isn’t only for criminals
• The iceberg: the difference between the surface web, the deep web, and the dark web
• How the 2023 23andMe breach exposed information on 6.9 million people because some customers reused passwords
• Two myths entrepreneurs believe: “I don’t make enough money to worry about it” and “I would know if I got hacked”
• Three simple steps you can take this week to protect yourself

Resources mentioned:

• Check whether your email has been in a breach: haveibeenpwned.com
• Take the free Are You Hackable? quiz
• Book a Single Security Assessment
• Register for our free October 28 training, “Protect the Business You’ve Built,” on phishing and staying safe online

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9

Some of the most important things we’ve built aren’t businesses. They’re our kids. Heather shares 15 years of lessons on keeping kids safe online, from Club Penguin in the living room to teens on Discord.

You’ll hear about:

• Why we block strangers when kids are young, then shift to educating them as they grow, with oversight the whole way
• Layers of protection: filters, device controls, and in-game settings
• Why your kids shouldn’t game on your work computer
• Four rules every kid should know
• Why open communication is the real safety net

This week’s challenge: Ask your kid to show you one app or game they love, and just listen.

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9

Privacy and security get used like they mean the same thing. They don’t. Treating them as one can leave a gap in your business you don’t even know is there.

In this Cybersecurity Awareness Month episode, Heather introduces Sarah. Sarah is a coaching founder who has done a lot right: a password manager, a reputable CRM, a properly set-up Google account. Her tools are secure. But her intake form collects information she never uses, her session notes live in her phone’s notes app, and sensitive client texts stay on her phone forever. Sarah never asked the privacy questions.

Heather explains the difference simply. Privacy is about what data you collect and who gets to see it. Security is about how you protect it. You need both to protect the business you’ve built.

In this episode:

• Clear definitions of privacy and security, and why they get mixed up
• Why you can have security without privacy, but you can’t really have privacy without security
• Why losing client data hurts more than losing your own, and what it costs in trust, renewals, and referrals
• The overlooked places client data lives: notes apps, old intake forms, texts, DMs, and voice messages
• Why “I’m too small to be a target” is a myth, and why being small can make you more of a target
• A brief look at privacy laws (GDPR and US state laws), including why your prospects’ locations matter too (not legal advice)

Your two moves this week:

• Privacy move: List every place client information shows up in your business. Then simplify. Consolidate tools that do the same job, and get your data out of accounts you haven’t opened in six months.
• Security move: Turn on multi-factor authentication for your CRM and your email.

Your reflection prompt:

If a client asked you to show them every place their information lives in your business, could you do it?

PDRM Consulting's mission is to help businesses reduce risk, specifically in the fields of Cybersecurity and Product Management.

Heather bridges the professional development gap in the corporate space by empowering growth-driven product managers to transition into strategic, results-oriented leaders. By focusing on enhancing key skills and decision-making capabilities, she helps them accelerate their leadership journey, achieve measurable outcomes more quickly, and excel in driving product success. Her approach ensures they thrive in their roles and unlock their full potential as impactful servant leaders within their organizations.

You can follow us for more daily content:

Instagram: @pdrmconsulting

LinkedIn: https://www.linkedin.com/company/pdrm-consulting

Join our Newsletter:https://solitary-block-17987.myflodesk.com/ofo6k6a0f9