[Starter Kit] Step 4: First Hires & Stop Copying Playbooks
Include: 2 Hiring Scorecards, Recipe Development Journal & Case Studies
Alright, so Step 1? You locked in your ICP, broke it into mini-segments, and mapped out your personas (missed it? go check it out here).
Step 2? You wrote problem-first messages that actually make people want to reply (missed that one too? it’s right here).
Step 3: Build your first stack, time to put it all in motion and actually launch your outbound. (missed it? go check it out here).
Your outbound program is burning through runway with nothing to show for it. You've hired expensive SDRs, invested in the "right" tools, and copied the same playbooks that worked for Gong or some LinkedIn gurus. But six months in, no pipeline, your board is getting anxious, and that promised outbound revenue engine feels like a mirage.
The harsh reality?
You're making the same two fatal mistakes as 80% of failed outbound programs: hiring the wrong people first and blindly copying playbooks that worked for completely different companies. Every day these mistakes continue costs you precious runway, market share, and team morale, while your competitors are figuring out what actually works.
Today's guide gives you the recipe to avoid both traps.
First, learn the exact hiring sequences used by Snowflake, Brex, and Rippling to build outbound engines that actually work, including which specific role to hire first based on your market.
Then, how to build the high-velocity experimentation engine that finds your unique outbound recipe in weeks instead of months. Stop burning cash on strategies designed for someone else's business and start building an outbound system engineered for your specific reality.
If you’re a paid member (or if you start a free trial), I added a few extras for you at the end of the newsletter:
2 hiring scorecards:
→ One for early SDRs
→ One to test if your outbound leader can actually do the job
Case Studies to vet your first SDR and AE hires (with email + cold call role plays)
And my go-to tool: the Recipe Development Journal, so you can track what’s working (and what’s not) in your outbound motion
Let’s get cooking!
Part 1: The First Outbound Hires
Most founders waste 6 months and hundreds of thousands in salary on outbound teams that generate zero pipeline. Why? They hire the wrong person first.
Your runway is burning while you wait for outbound results that never come. Your board is asking tough questions. Your AEs are starving for meetings. And worst of all? That expensive SDR leader you hired is already blaming your "messaging" and "ICP" instead of delivering results.
Learn which role to hire first based on your specific market, the blueprint for each essential role, and the proven path that turns your first outbound hire into predictable pipeline within 90 days instead of endless experimentation.
1. Who Do You Hire First? Market-Based Hiring Sequences
Who Do You Hire First? Your Market Dictates Your Outbound Sequence
73% of failed outbound programs made the same mistake—they hired the wrong person first for their specific market.
Market-Based Hiring Sequences That Work
Your market and business model determine your optimal first hire, not generic best practices. The wrong sequence burns runway with zero pipeline to show for it.
Large TAM targeting SMB?
Start with a GTM engineer to run programmatic email campaigns, then add SDRs once the system works to manage responses. Snowflake and Rippling followed this exact playbook, scaling efficiently by automating outreach first before adding headcount.
Heavy phone focus or small TAM enterprise?
Begin with 1-2 experienced SDRs, then add a fractional GTM engineer to support them with verified data and efficient list-building. Owner.com (targeting restaurant owners) and Brex prioritized human touchpoints in their earliest outbound motions.
These principles apply across all successful outbound programs:
Never hire junior SDRs for an unproven motion
Don't hire SDRs without a sales leader to manage them
Focus on experienced talent who can execute while learning
The 2 Proven Paths to Outbound Success
Path 1: The Conservative Approach (Lowest Risk)
Your VP of Sales hires 1-2 experienced SDRs first who are:
Focused on execution and learning, not just meeting quotas
Actively managed by the VP of Sales, not left to figure it out
Only scaled once outbound consistently generates pipeline
This prevents the common trap where founders rush to hire a senior outbound leader who quickly builds a team before validating strategy, ICP, and messaging, burning months of runway with little to show for it.
Path 2: The Experienced VP + Player Coach Approach.
When your VP of Sales has:
Already built multiple successful outbound teams
A proven playbook for your specific ICP and ACV range
Strong conviction backed by your full support
And they know a Player-Coach Approach (Outbound Leader)
Willing to be the first SDR themselves (not just managing)
Ready to build systems, test messaging, and run outreach personally
Only hiring once they've proven pipeline can be generated
6 Real-World Success Stories
These hiring sequences aren't theoretical, they're backed by companies that've successfully scaled outbound:
When Matt Plank (Current CRO) joined Rippling as employee #5, he built sales from scratch: cold calling, emailing, and closing deals himself. Once he saw traction, he hired SDRs and AEs from his network and scaled using programmatic outbound as the core growth engine.
Chris Degnan (Ex-CRO), Snowflake’s first sales hire in 2013, joined a 15-person product-focused team. He aimed for 8 meetings a week, hired an intern, built email lists by hand, and sent 2,000 cold emails weekly.
Brex:
When Sam Blond joined as CRO, he inherited 2 AEs and hired 4 more with a strong outbound focus. He then brought on a Director of BDR he knew personally, who critically was willing to be the first hands-on BDR herself before building a team of 3 experienced SDRs from his network.
Owner.com:
At $2M ARR with 4 AEs, they hired their first BDR to prove the outbound model by focusing on closed-lost opportunities. Only at $3M ARR did they add contractors for enablement and operations, which became full-time positions at $4-5M ARR.
Mosaic (acquired by HiBob):
The CEO hired Matt Roberts (my former boss at Chili Piper) as SDR director to build their outbound program personally before adding a single BDR, eventually scaling to a team of 10.
Oh and by the way, I recorded a podcast with Matt where we unpack exactly how he pulled it off. Go give it a listen if you want all the behind-the-scenes.
Also, Matt just launched a new show: Top Shelf: The Outbound Leadership Podcast. Honestly? It’s the kind of podcast I wish I had back when I stepped into my first manager role. Got to listen to it here.
Hockeystack:
After building initial sales with inbound only, they hired Alex Choi, a Head of SDR to build their outbound function from scratch, doing the work personally before hiring the first BDRs.
2. Role Blueprints: Your Early-Stage Outbound Team
Now let's talk about each roles for early stage outbound your first hires, you might not have a strong onboarding process and enablement team to cut ramp time and have them fully productive.
2.1 The Outbound SDR
Your first SDRs make or break your outbound strategy. Hire for experience, and potential.
For early-stage companies with unproven outbound motions, hire SDRs with 6-24 months of SaaS, agency prospecting, or recruiting experience. Source candidates through your network, your SDR leader's network, and referrals from AEs or investors. Why from network? Because you don't have a track record of experience to go off of the way that you do. Using your network will help vet to hire the right candidates and reduce your chances of mis-hiring.
The ideal profile combines technical skills with crucial soft traits:
Coachability and curiosity (do they research your company deeply?)
Persistence and grit (outbound is relentless rejection, especially early-stae)
Adaptability to thrive in your chaotic environment
Tech-savvy and AI-savvy (can they use Clay, Zapier, and other tools?)
Self-starter that doesn't need constant direction
Creativity
For compensation in 2025, structure pay with 70-80% base ($55-70K) and 20-30% variable ($25-35K) for an OTE of $80-100K. This base-heavy model reduces churn risk while your program matures.
Common mistakes with early-stage SDRs:
Hiring: With no experience, the learning curve will be steep. Boards and founders won’t wait 12+ months to see results from your outbound program.
Hiring SDRs from big famous companies: They can be strong, but the problem: You need to assess if they can unlearn old routines or bad habits and adapt to your company’s environment.
Here’s an example:
We hired an SDR who was #1 at a big company with 200+ reps. But when they joined us, they couldn’t perform. Why? Because success at one company doesn’t always mean they’ll crush it at yours. Because big SDRs team has more resources so a lot of reps get complacent with way to get everything.
P.S. If you’re about to hire your first SDR, I added a scorecard and a real case study at the end of the newsletter. Scroll down and check it out.
2.2 The Player-Coach SDR Leader: Builder, Not Just Manager
The right leader builds while doing, not just directing. Hire for execution, not management.
Your ideal SDR leader at this stage is a player-coach who has 2+ years of consistently beating SDR quota and 6-12 months of team leadership experience. They must be willing to be your first SDR themselves, building the system and testing messaging before hiring others.
Companies like Brex, Hockeystack, and Mosaic succeeded by hiring outbound leaders before hiring SDRs who personally built their outbound programs first, then scaled teams only after proving pipeline generation. This approach reduced risk and accelerated results.
The best SDR leaders are systems thinkers who can both execute personally and build repeatable processes that scale beyond themselves.
P.S. If you’re thinking about hiring your first outbound leader, I dropped a full case study at the bottom of the newsletter. Give it a look.
2.3 The Outbound Account Executive: Not Order-Taker
Outbound AEs who built their own cold calling muscle close 40% more deals than those who've only worked with inbound leads.
Your early outbound AEs must have proven experience closing similar deal sizes and sales cycles at companies of a comparable stage. The most successful AEs have hands-on outbound prospecting experience (often as former SDRs) AND closing outbound deal experience. Which helps them understand the full journey from cold outreach to closed deal. When Brex scaled from $0 to $100M, Sam Blond specifically hired AEs with strong outbound backgrounds who could handle the unique challenges of deals that didn't come inbound.
Look for these critical traits:
Outbound DNA: Former SDRs or AEs with outbound experience understand the full buyer journey
Playbook Makers, Not Followers: Skip candidates who ask "where's the playbook?" and hire those excited to build it
Entrepreneurial Spirit: Choose an entrepreneur with sales experience over industry veterans, their sales fundamentals and hustle accelerate product/market fit
Context-Appropriate Skills: Match your sales model, consultative experts for enterprise/high-ACV or transactional closers for high-velocity/low-ACV
Soft Skills Foundation: The same traits as your SDRs, coachability, persistence, adaptability, but with proven closing ability
Avoid these common pitfalls:
Order Takers vs. Deal Makers: Inbound "order takers" often collapse when facing the resistance and objections common in outbound deals
Resume Hires: Famous company names on resumes often mask mediocre performers who rely on brand strength
Closing-Only AEs: Early-stage outbound requires versatile players who understand prospecting mechanics
Self-Sourcing Expectations: Don't expect new AEs to source 50%+ of pipeline while also closing effectively in Year 1
The best outbound AEs aren't polished corporate closers, they're scrappy, adaptable builders who thrive when creating structure from chaos and can navigate the unique buyer journey who didn't ask to be sold to.
P.S. If you’re about to hire your first AEs, I added a cold outreach case study at the end of the newsletter. Scroll down and check it out.
2.4 The Supporting Cast: Operations Systems That Scale Revenue
Companies that invest in operations support by $3M ARR scale 2.5x faster than those that wait until $10M.
I learned this lesson directly from Kyle Norton, CRO of Owner.com, who learned the hard way: scaling sales teams without a GTM engineer, RevOps and enablement creates painful bottlenecks, slow onboarding, struggling reps, and messy data that eventually causes growth to stall. Even with a small team, these support functions build the engine of your business, the CRM processes, account scoring dashboards, and training systems that prevent chaos as you grow.
Why invest early when cash is tight?
Multiplied Rep Productivity: Support functions make your expensive AEs and SDRs 30%+ more productive
Systems-Based Growth: Without proper systems, companies might "brute force" their way to a couple million in revenue, but then experience a "really bad stall out" as the sales leader becomes removed from individual reps
Faster Onboarding: Early investment in enablement reduces ramp time from 6+ months to 60-90 days, allowing new hires to hit quota right away
The smart approach isn't hiring these roles full-time immediately (a $200K+ investment). Instead, follow this implementation strategy:
Start with Contractors: Begin with trusted fractional support working 10-15 hours per week until your ARR can justify full-time roles
Vet Carefully: "This space is full of 'consultants' who don't know what they're doing. Vet them hard," warns Kyle
GTM Engineer: Your Automation Architect
Your outbound approach determines when and how you use this role. For companies with a large TAM targeting SMB via email, a GTM Engineer can build your programmatic outbound system from scratch. For small TAM or phone-focused strategies, they boost rep efficiency through data enrichment and workflow automation.
Start part-time ($150-250/hr) and move to full-time around $5-10M ARR when you have 10+ reps. As Brendan Short notes in his newsletter The Signal, premature investment wastes resources, but waiting too long creates scaling bottlenecks that are hard to fix.
RevOps: Your Systems Builder
RevOps builds the foundation that makes everything else work, from lead routing to accurate forecasting.
Bring in fractional support ($125-175/hr) around $1-2M ARR to audit your CRM and build dashboards. Move to full-time around $3-5M ARR when forecasting and pipeline management become mission-critical.
Enablement: Your Performance Multiplier
Start with a manager or senior rep spending 20-25% of their time on coaching and playbooks when you reach 5-10 reps. Transition to full-time around 20-30 reps or when moving upmarket to enterprise deals.
These supporting functions solve problems from the rep's perspective, not top-down, and have experience carrying a quota themselves. This ensures they build practical tools that actually help close deals, not theoretical frameworks that gather digital dust.
Without these supporting functions, your outbound engine will break down just as it begins to generate momentum. These investments create the foundation that makes "everything downstream better" and ultimately drives sustainable growth.
3. The Path to Outbound Success
Start with proven talent: Experienced SDRs or player-coach leaders who can execute while building, not junior reps who need extensive support.
Match your first hire to your market: GTM engineer first for high-volume SMB; experienced SDRs first for high-touch enterprise
Choose the right sequence for your reality: Consider your existing team, leadership experience, and customer profile
Build infrastructure before you think you need it: Fractional ops, enablement and GTM engineering prevent the scaling bottlenecks that kill momentum.
Insist on validation before scale: Whether through player-coaches or experienced reps, prove the model works before building a team
Your first outbound hires are the most consequential revenue decision you'll make this year, take the time to get it right.
Part 2: Stop Copying Playbooks: Most Early-Stage Outbound Fails Within 90 Days
Your outbound program is sputtering while your competitors seem to be crushing it. You've implemented the same "proven playbooks" from Gong podcasts and LinkedIn gurus, but your SDRs are generating zero pipeline and your runway keeps burning.
Every day without a functioning outbound engine is another day your competition is stealing market share. Your board is asking why meetings aren't happening, your SDRs are getting demoralized by constant rejection, and you're starting to wonder if outbound even works for your business. Meanwhile, that expensive consultant you hired keeps saying "just give it time" while your cash reserves dwindle.
This guide reveals the three operating principles that actually drive early-stage outbound success, without copying someone else's playbook. Learn how to build a high-velocity experimentation engine that discovers your unique outbound recipe in weeks instead of months, focus on the one North Star metric that truly matters, and replace endless opinion-based debates with objective frameworks that accelerate learning. Your path to predictable outbound pipeline isn't about finding the perfect tactic, it's about building the perfect learning machine.
1. Own One North Star Metric That Drives Everything
Mature outbound teams track dozens of metrics, but early-stage startups thrive on extreme simplicity.
For most early-stage teams, Sales Qualified Opportunities (SQOs) should be your singular focus, aim for 10-20 per month per SDR.
SQO could be using the companies you want to meet with for your experiments. Not using a qualification like BANT to qualify an opportunity.
Tracking this one metric eliminates distraction and creates clear accountability. When you're still discovering what works, quantity beats quality every time. You lack the historical data to know which accounts/segments/personas will convert best, so prioritize volume until patterns emerge.
When repeatability happens, the quality conversation begins. If AEs start complaining about poor-fit meetings or calendar congestion, that's your signal to evolve metrics, shift to revenue focus for SMB or Stage 2 opportunities for enterprise.
Winning measurement framework:
1. Email / LinkedIn DM (Big-TAM, programmatic)
Open Rate: 30-45 % (warm domain)
Positive Reply %: 0.8-1.5 %
Demo / Positive Reply: 25%+
2. Cold Calling (Small-TAM or Phone-First)
Stage KPI: Dials / SDR / Day:
Connect Rate(Connected calls ÷ dials): 5%+
Convo → Meeting Rate(Meetings ÷ connects): 10%+
Your North Star creates the foundation for everything else, choose it wisely and guard it religiously.
2. Build a High-Velocity Experimentation Engine
High-performing outbound teams don't avoid failure, they systematically fail faster than competitors.
The average startup wastes 3-6 months running a single outbound playbook before declaring it "doesn't work." Meanwhile, elite teams test 6-12 micro-hypotheses in the same timeframe, discovering exactly what resonates with their market. These teams recognize that speed of learning trumps perfection of execution. Instead of debating which approach might work, they test multiple approaches simultaneously in controlled experiments.
ElevenLabs Example (if I was leading outbound at ElevenLabs):
Instead of spending weeks perfecting a campaign targeting media production companies, I'd launch two competing hypothesis tests simultaneously:
Test A: Media producers care most about voice quality and naturalness
Test B: Media producers care most about production speed and cost savings
Each test would target just 100 accounts with slightly different messaging, allowing us to quickly determine which resonates better before scaling to our full database.
The 2-Week Sprint Model accelerates discovery:
Week 1 – Ship Fast: Select ONE hypothesis Monday, build two messaging variants Tuesday, deploy to 100-account sample Wednesday
Week 2 – Learn Faster: Review preliminary data Monday, check metrics Thursday, make go/no-go scaling decision Friday
This high-velocity approach means ElevenLabs could simultaneously test whether media producers care most about voice quality or cost savings, with real-world data deciding the winner, not opinions.
Commit to testing just one meaningful variable at a time, but test it quickly and decisively.
3. Replace Opinions With Objective Scorecards
Early-stage outbound teams can waste months in circular debates about target segments and messaging.
Successful teams replace subjective debates with data-driven frameworks like ICE (Impact, Confidence, Ease) scoring. This objective approach forces you to evaluate experiment ideas on their merits, not by who proposed them. By ranking your backlog of hypotheses, you ensure your limited resources target the highest-potential opportunities first.
The ICE scoring method works across experiment types:
Mini-Segment: Testing a vertical or company size
Messaging
Channels: phone, email, Linkedin, direct mail, mini-websites
Breadcrumbs (Digital data points)
Increase conversion rate
Data quality: testing a new data provider
Number of prospects reached by accounts
Number of touch before stopping reaching out
etc
You don't need enterprise tools to implement this methodology. A simple spreadsheet and disciplined weekly reviews create the structure for high-velocity learning. The framework eliminates emotional attachment to ideas by grounding decisions in objective measurement.
When opinions clash, let data be the tiebreaker that moves everyone forward.
P.S. I built a Recipe Development Journal, a simple way to track and improve your outbound experiments. You can get it at the end of the newsletter.
ElevenLabs Example:
Our experiment board would include tests like:
"Game studios prioritize multilingual character voice generation"
"Content creators value workflow integration over voice quality"
Each card contains the hypothesis, metrics to track, and sample size.
Key Takeaway
The outbound recipe that works for your company can only be discovered through systematic experimentation. Instead of copying someone else's playbook, build your own high-velocity testing engine to find your unique path to outbound success.
Success isn't about avoiding failures, it's about increasing your experiment velocity so the winners you discover can scale quickly enough to drive meaningful revenue growth.
Three Principles That Drive Early-Stage Outbound Success
Single-metric clarity creates focus when everything feels urgent but resources are limited
Systematic experimentation discovers your unique outbound recipe faster than copying others' playbooks
Objective frameworks prevent opinion-based debates and accelerate decision-making
Stop searching for the perfect playbook, start building your outbound learning machine instead.
Bonus: additional Resources for this guide:
Below you will get 4 resources for your first hires and track your experiments (Notion Docs):
2 Hiring Scorecards:
Early-Stage Outbound SDR
Outbound Leader (The Player-Coach Test)
Case studies for your first SDR/AE hires: Email + Cold Calling Role Play
The Recipe Development Journal: Track Your Outbound Experiments
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