Sales Enablement Lead

Hi! 👋 I’m Val, VP of Sales at TLDR. I’m looking for a Sales Enablement Lead to join us and help accelerate growth across our sponsorship business by making our sellers more effective, faster. You’ll be working directly with me as we shape how TLDR partners with the biggest names in tech and media.

Who We Are

TLDR is a collective of technical newsletters on startups, software engineering, AI, cybersecurity, marketing, product management, and more, with over 6 million subscribers growing 100% year-over-year.

Our mission is to build the paper of record for the tech industry—the trusted source that people who work in tech rely on to inform them about important trends and developments.

About the Role

We're looking for someone who can build onboarding, training, and sales enablement content that has a direct and measurable impact on revenue. You’ll be responsible for reducing ramp time, helping close larger deals, and ensuring every seller at TLDR has the right tools, materials, and talk tracks to win.

This is a highly cross-functional role reporting into the Sales org. You’ll work closely with Account Executives, Account Managers, SDRs, and Leadership.

What You’ll Do:

• Build onboarding and training programs to ramp new hires faster

• Create sales collateral, talk tracks, objection handling guides, and competitive intel

• Partner with Sales, AM, and Marketing to design high-impact playbooks

• Analyze what’s working and what’s not across the funnel, and build content that closes gaps

• Maintain and scale enablement materials in a way that supports TLDR’s growth

• Enable the team to speak confidently to our media offerings and ad formats

• Drive improvements to deal size and close rate through better tools and training

About You

• 2–10 years of experience in sales enablement or GTM enablement roles

• A track record of promotions and impact in past roles

• Deep experience in media or ad sales — this is a must

• Strong insights on how to onboard new hires at early-stage companies

• Experience building out enablement from scratch at a startup

• Proven ability to tie enablement work to revenue outcomes

• Skilled at building materials that AEs and AMs actually use

You're Not a Good Fit If You:

• Lack media or ad sales experience

• Have only worked at large, structured companies

• Don’t focus your enablement work on measurable revenue impact

Interview Process

We like to keep things fast, focused, and human. Here's what to expect:

1. Recruiter Screen w/ Brandon
We’ll confirm baseline fit and screen for relevant media experience, startup exposure, and revenue orientation.

2. CEO Interview w/ Dan Ni
A conversation with our CEO to assess startup scrappiness, strategic thinking, and how you approach high-impact work.

3. Written Assessment
You’ll create a 1-page “Selling B2B Media 101” doc to help onboard a new AE from SaaS who’s unfamiliar with media sales.

4. Interview w/ Val
A deep dive on onboarding strategy, playbook development, enablement content, and how you’ve moved the needle in past roles.

5. Final Panel Presentation w/ Dan & Val
You’ll use our media kit and case studies to create:

• A 1-pager for AI startups interested in advertising with TLDR

• A 10-minute training session with discovery questions, talk tracks, objection handling, and a pitch structure for new AEs

Why You'll Love It

• Competitive base salary plus additional performance-based compensation

• 100% remote company with a shared sense of purpose

• Annual team offsite — August 2025, location TBD!

• Unlimited PTO — most team members take 2–3 weeks off per year plus holidays

• 401(k) plan

• Comprehensive medical, dental, and vision benefits with a 100% paid option

• Paid parental leave

• Hardware stipend — MacBook Pro M4, monitor, headset, chair included

• Software, Learning & development stipend — we’re a curious group that values growth

• Contemporary tech stack and tools — we embrace and expect automation

• Autonomy and agency to contribute to the growth of one of the largest tech newsletters in the world

What We Value

• Urgency and bias to action

• Iterative improvement

• Clear communication

• Integrity

• Resourcefulness

If you need any accommodations in the interview process, please let us know.