Director of GTM Strategy & Enablement

Summary

Are you a collaborative, strategic sales enablement professional who loves bridging sales and marketing? Do you excel at guiding partners to create effective, innovative sales strategies and collateral? October Three, a pioneering, team-oriented financial services company, is recruiting for a Director of GTM Strategy & Enablement; Peoplr is excited to be leading this search.

In this role, you will lead bottom‑of‑funnel marketing and sales enablement efforts, developing high‑impact campaigns, content, and sales tools that improve conversion and support revenue growth. You’ll also support retention initiatives, brand integration for newly acquired firms, and ongoing optimization of data, systems, and cross‑team processes. Additionally, you’ll produce polished creative assets and ensure all communications uphold a unified, professional brand experience. This is a full-time, regular position, and can be worked fully remotely or hybrid out of the company’s locations in Chicago, IL, Irving, TX, or Jacksonville, FL.

About October Three

October Three is a defined benefit retirement firm made up of actuaries, consultants and administration experts. They have developed unique, one-of-a-kind software to handle the future of defined benefit plans. Their mission is to ensure that all people feel prepared for retirement both financially and emotionally, and they strive to develop sustainable solutions that work for both employers and employees. Culturally, they are very team oriented with strong collaboration among colleagues to provide the highest quality service to our clients. They are an entrepreneurial, fast-growing company with lots of opportunities for growth, cross training, upward mobility, and professional development.

This position offers…

• Competitive salary ($120k-150k) and bonus opportunities
• Comprehensive benefits including medical, dental, vision, short and long-term disability, life insurance, HSA, FSA, employee assistance programs, PTO, 401(k), and a cash balance pension plan
• Opportunity to launch a dedicated sales enablement function and further define what this looks like for the company

Must Haves

• 7-10 years of experience in B2B marketing, sales enablement, and/or sales; proven successful track record in sales enablement, partner marketing, or customer lifecycle marketing
• Industry experience within financial, banking, benefits, healthcare, and/or professional services
• Familiarity with CRM tools, data, and pipeline analytics; data-driven with ability to translate metrics into strategy
• Proficiency in PowerPoint and light design tools (Canva, Adobe, etc.)
• Strong strategic and creative thinking; able to turn business objectives into actionable programs
• Project management excellence – capable of managing multiple stakeholders and priorities in a fast-paced, quick turnaround environment
• Bachelor's degree or equivalent experience

Nice-to-Haves

• Prior direct sales or financial advisor experience
• Experience working with advisory networks or channel partner systems a major plus

All positions at October Three Consulting require an applicant who has accepted an offer to undergo a background check. Background checks may include some or all the following: SSN validation, education verification, employment verification, and criminal check. By applying for a position with October Three, you understand that you will be required to undergo a background check should you be made an offer. You also understand that the offer is contingent upon successful completion of the background check and results consistent with October Three’s employment policies.

About Peoplr

Peoplr is a national Human Resources consulting firm made up of HR experts enabling businesses to transform into engaging workplaces where people deliver outstanding results. Check us out on our website at: www.mypeoplr.com

Peoplr is proud to be an Equal Opportunity Employer. All applicants will receive consideration for employment, as Peoplr does not discriminate against an individual because of their race, color, religion, gender, sex (including same sex, gender identity, and sexual orientation), pregnancy, parental status, marital status, national origin or ancestry, age, physical or mental disability, sickle cell trait, genetic information and testing (including family medical history), AIDS/HIV status, source of income, political affiliation, military service, other non-merit based factor, or any other characteristic protected under applicable federal, state or local law.

Peoplr is committed to providing equal opportunity and reasonable accommodation for people with disabilities. Accommodation for applicants with disabilities is available upon request in connection with the recruitment process. If you require a reasonable accommodation to complete an application, interview, or otherwise participate in the recruiting process, please call us at 844-577-1940 or send us an email at recruiting@mypeoplr.com