Head of Sales Enablement

Overview

You'll design and deliver training programs for financial advisors at 49 Financial, an independent RIA growing through regional expansion and recruiting both early-career advisors and experienced reps approaching retirement. You'll work closely with the EVP of Growth and field leadership to onboard new hires, standardize sales processes, and help advisors navigate the transition to an independent model. Most of your time goes to building curriculum, delivering training sessions, and riding along with reps to see what's actually working.

Role Snapshot

Company Context

Stage: Private/Established (275 employees, actively scaling)

Size: 275 employees

Growth: Launching new regions, hiring across experience levels, building out field infrastructure

Market Position: Independent RIA competing for advisor talent against wirehouses, other RIAs, and broker-dealers

GTM Reality

What 49 Financial Does: 49 Financial is an independent Registered Investment Advisor. Their "customers" are financial advisors who affiliate with them to serve end clients. The GTM motion here is two-fold:

1. Recruiting advisors (both new and experienced) to join 49 Financial
2. Enabling those advisors to grow their books of business

Your Focus: You're not selling to end clients—you're enabling advisors to do that. You'll support advisors who are:

• New to the industry (need foundational training on prospecting, client meetings, planning tools)
• Transitioning from other firms (need help adapting to 49's platform, compliance, and operating model)
• Growing their existing books (need advanced training on complex planning scenarios, practice management)

Common Challenges:

• New advisors struggle with prospecting and closing their first clients
• Experienced advisors resist "the way we do things here" if they came from a different firm culture
• Regional expansion means you're training people you can't always see in person

What You'll Actually Do

Time Breakdown

Program Development (35%) | Training Delivery (30%) | Field Collaboration (20%) | Admin/Reporting (15%)

Key Activities

• Build onboarding curriculum: Create standardized training for new advisors—prospecting scripts, CRM workflows, compliance basics, product knowledge. You'll be updating this constantly as the firm adds tools or changes processes.
• Deliver training sessions: Run virtual and in-person workshops for new hires and existing advisors. Topics range from "how to run a first client meeting" to "complex estate planning scenarios." You'll do some big group sessions and some one-on-one coaching.
• Ride-alongs and coaching: Spend time in the field with advisors—join client meetings, listen to prospecting calls, review their pipelines. This is where you figure out what's actually working vs. what sounds good in a training deck.
• Cross-functional projects: Work with compliance, operations, and marketing to align on what advisors need. Lots of meetings to translate "here's what field leadership wants" into "here's what's actually possible."
• Content creation: Build job aids, playbooks, recorded training videos. You're constantly creating reference materials that advisors can use when they forget what you taught them.

The Honest Reality

What's Hard

• Diverse audience: Training a 25-year-old new advisor is completely different from training a 60-year-old with 30 years at Morgan Stanley. You need to make both feel like you're adding value.
• Measuring impact: It's tough to prove that your training is why an advisor hit their goals vs. them just being good at their job. You'll spend time fighting for budget and headcount.
• Regional expansion chaos: New regions mean new leaders with their own ideas about "how we should train people." You'll negotiate a lot to keep things standardized while respecting local needs.
• Adoption is always a battle: You'll build great training content that some advisors ignore. Getting people to actually use what you teach them is harder than building it.
• You're in the middle: Field leaders want more training; executive leadership wants proof of ROI. You're constantly balancing "give us everything" with "show us it's working."

What Success Looks Like

• New advisors ramp to productivity 20-30% faster (measured by time to first client, assets under management growth)
• Training completion rates hit 85%+ for mandatory programs
• Field leaders stop building their own rogue training materials because yours is better
• Advisor satisfaction scores on training quality are consistently high
• You're invited into strategic conversations about growth because leadership trusts your view of what's happening in the field

Who You're Supporting

Primary Audience:

• New financial advisors (0-2 years experience): Need foundational sales training, tools training, confidence-building
• Experienced advisors transitioning in (10+ years at other firms): Need help adapting to 49's systems, compliance differences, and culture
• Field leaders (Regional VPs, Branch Managers): Need your help coaching their teams and identifying skill gaps

What They Care About:

• New advisors: "Will this training actually help me get clients and not embarrass myself?"
• Experienced advisors: "Is this a waste of my time or will I learn something I don't already know?"
• Field leaders: "Will this move the needle on my team's production numbers?"

Requirements

• 7-10+ years in financial services, ideally including time as a producing advisor or sales leader (they want someone who's "been in the chair")
• Experience building and delivering enablement programs, preferably in wealth management or financial advisory
• Strong cross-functional collaboration skills—you'll be working with compliance, ops, tech, marketing, and field leadership constantly
• Comfortable with ambiguity and figuring things out as the firm scales into new regions
• Willingness to travel to regional offices and ride along with advisors in the field
• Credibility with experienced advisors (they need to respect that you've done the job, not just taught it)