When should you actually hire for your DTC brand? Connor Gross from Constant Hire has recruited hundreds of roles for consumer brands scaling from $0 to $500M—and his #1 rule might surprise you: hiring should be your last resort.

Connor Gross — Founder at @ConstantHire, recruiting exclusively for consumer brands.

In this episode, Connor breaks down his complete hiring framework:

→ Why hiring too early kills bootstrapped brands

→ The 4 revenue stages that change your hiring strategy ($0-1M, $1-10M, $10-100M, $100M+)

→ Freelance vs agency vs full-time: when each makes sense

→ How to find undervalued talent (the arbitrage strategy most founders miss)

→ Which roles to prioritize at each stage (ops, creative, retention, growth)

→ Common candidate experience mistakes that kill your best hires

If you are a DTC founder or operator at $500K-$20M trying to figure out your next hire—whether that's your first employee, transitioning from agency to in-house, or building out your growth team—this episode will save you from expensive hiring mistakes.

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ABOUT KARTWORTHY

Kartworthy is a media brand for DTC and ecommerce operators generating $1-20M in revenue. We deliver tactical, data-driven insights from operators and agency experts—no fluff, just frameworks you can implement this week.

Hosted by Matt Lady, Associate Director of Ecommerce Marketing at KlientBoost.

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LINKS

Constant Hire: https://www.constanthire.com/

Connor on LinkedIn: https://www.linkedin.com/in/connor-j-gross-/

KlientBoost: https://www.klientboost.com/expertise/ecommerce-marketing-agency/

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If you want help scaling your eCommerce/DTC brand with Media Buying, Ad Creative, SEO, CRO, and Business Intelligence — hire us at klientboost.com — a marketing agency with aggressive accountability & proactive obsession.

Timestamps:

0:00 When hiring actually kills your brand

1:14 The hiring decision framework: time vs knowledge

3:18 $0-1M stage: Find undervalued talent (overseas arbitrage strategy)

5:23 $1-10M stage: Ops support + ecommerce manager (the generalist approach)

8:10 When to hire your first specialized role

11:42 $10-100M stage: The shift to in-house specialists

16:28 $100M+ stage: Why agencies lose efficiency at scale

21:03 Freelance vs agency vs full-time decision tree

26:30 Candidate experience mistakes (test projects kill excitement)

28:34 The #1 cultural trait to look for: curiosity in the space

Most DTC brands convert only 10% of buyers into subscribers after the first purchase. But with the right first-order subscription optimization, you can hit 40% opt-in rates immediately. Matthew Holman, founder of Subscription Prescription, breaks down the architecture and testing strategies behind high-performing subscription offers.

Matthew Holman — Founder of Subscription Prescription | Known as "The Subscription Doc" | thesubscriptiondoc.com

What You'll Learn:

→ Why first-order subscription optimization outperforms post-purchase conversion (40% vs 10% opt-in rates)

→ The two critical components of subscription offers: what you get + how you present it

→ How 3-month bulk subscriptions achieve 10% higher renewal rates than monthly options

→ Why gifting beats discounting for margins and attracting better buyers

→ The 28-day billing cycle trap and how to align subscription frequency with consumption behavior

If you're a DTC founder or operator looking to scale subscriptions without killing margins, this episode delivers the tactical frameworks you need to test immediately.

if you want help scaling your eCommerce/DTC/CPG brand hire us at klientboost.com — a marketing agency with aggressive accountability & proactive obsession.

SIGN UP FOR THE 2026 ANNUAL PLANNING 12+ HOUR FREE LIVESTREAM MONDAY 12/15: http://ordnl.link/SOhsSme

Insurance companies are paying $10-14K for medical-grade kids' beds, and parents aren't paying a dollar out of pocket. This changes everything about how you structure your email strategy, bundle offerings, and lifecycle automation. In this episode, Samar Owais breaks down the exact email playbook she built for a medical device brand that creates beds for kids with special needs.

What You'll Learn:

→ Why bundle offers outperform discounts when insurance covers the cost → The 90-day customer journey from quiz to approval to purchase

→ How to write empathetic emails for sleep-deprived special needs parents → Why weekly nurture alone won't drive sales (and what will)

→ Accessory upsells that drive repeat purchases after a one-time big buy

→ The psychology of buying when someone else pays the bill

If you're a DTC founder, email marketer, or eCommerce operator trying to figure out high-AOV email strategies, niche market positioning, or lifecycle automation for complex purchase journeys, this episode gives you a complete playbook from a real client case study.

Connect with Matt:

https://x.com/mattlady

https://www.linkedin.com/in/mattlady/

The Performance Marketing Agency for eCommerce & DTC Brands: https://www.klientboost.com/

Find out more about Samar: https://samarowais.com

Take the Email Strategy Quiz: https://emailsdoneright.com/quiz

Check out the eCommerce Email Bootcamp: https://emailsdoneright.com/eebc-special-admission

00:00 Intro: Insurance pays $10-14K for kids' beds

01:39 Medical device brand scenario introduction

02:29 Samar introduces the client case study

03:45 Why bundle offers are the correct answer

05:15 Understanding the audience: parents vs. kids as users

06:30 The empathetic email approach for sleep-deprived parents

08:10 Importance of knowing your customer deeply

09:29 Additional products: pillows and accessories for repeat purchases

10:38 The 90-day purchase journey and qualification quiz

13:15 Post-purchase education and measuring success

15:45 Using testimonials instead of making medical claims

17:54 The power of social proof from exhausted parents

19:12 Compliance challenges with medical-grade products

19:50 Service guarantees and bed repair programs

20:33 Why 20% off discounts don't work for this brand

21:42 The role of weekly nurture emails in the strategy

22:24 Potential for secondary bed purchases

22:48 Final insight: knowing when buyer and user are different

23:11 Outro: Key takeaways and livestream announcement