What's up, it's Zayd.

Most B2B startups try to go straight to the top. CEO to CEO. Founder to founder. Makes sense, right? Decision makers talk to decision makers.

Wrong.

One of our customers just generated $400K in pipeline by doing the exact opposite. They targeted the middle and worked their way up. They broke into enterprise accounts that had ignored traditional top-down approaches for years, including a $10B global construction company.

This "middle-up" strategy is quietly revolutionizing how early-stage companies compete with established players.

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Why Top-Down Fails for Startups

Here's the brutal reality: C-level executives at large enterprises are insulated from startup outreach by design. They have assistants, strict communication protocols, and vendor management processes that filter out 99% of unsolicited contact.

Even when you break through, there's a fundamental mismatch. CEOs think strategically about quarterly initiatives and annual budgets. Your startup solution, no matter how great, rarely aligns with that level of thinking unless you're solving a board-level crisis.

Meanwhile, the middle management is drowning in operational challenges that your solution might solve immediately. They feel the daily pain your product addresses, and they're accessible through channels like LinkedIn.

The Middle-Up Case Study

Joseph Leiva from Kaster, a construction tech startup, discovered this by accident. Traditional cold calling to executives wasn't working. Their target buyers—VPs in risk, finance, accounting, and compliance—were reception-resistant but LinkedIn-responsive.

Here's what happened when they shifted strategies:

The Traditional Approach (Failed)

• Cold calling C-suite executives

• Pitching through official channels

• Relying on warm introductions

• Result: Limited success, long cycles

The Middle-Up Approach (Succeeded)

• Targeted VPs and directors through LinkedIn

• Focused on operational pain points

• Built relationships with daily users

• Result: $400K pipeline in 60 days

The breakthrough moment was getting a response from a director at that $10B construction company. Someone Joseph had connections with at the top, but the traditional path hadn't worked. The middle manager who actually used similar tools daily was immediately interested.

That conversation led to executive introductions, corporate demos, and enterprise-level deals.

Why Middle-Up Works

Pain Proximity Middle managers feel the daily friction your solution solves. They're thinking about this week's problems rather than strategic initiatives. If your product makes their Tuesday easier, they care.

Decision Influence While they might not have final budget authority, middle managers heavily influence purchasing decisions. When they advocate upward for a solution, executives listen because these are the people dealing with operational reality.

Accessibility Directors and VPs are active on LinkedIn, respond to thoughtful messages, and engage with industry content. They're accessible in ways that C-suite executives simply aren't.

Implementation Ownership Even if the C-suite approves a purchase, middle management typically owns implementation. Getting them excited early creates internal champions who ensure successful deployment.

The Implementation Framework

Step 1: Identify True Users 

Target daily users. Who actually experiences the problem you solve? Who would use your solution day-to-day? Those are your primary targets.

Step 2: LinkedIn-First Outreach 

Email fatigue is real, especially at enterprise level. LinkedIn allows for more personal, professional outreach that feels less like spam and more like networking.

Step 3: Pain-Specific Messaging 

Focus on operational challenges. Instead of "transform your business," try "eliminate manual reporting" or "reduce compliance preparation time."

Step 4: Build Internal Networks 

Once you connect with one middle manager, ask about their team, cross-functional partners, and related departments. Map the internal ecosystem.

Step 5: Executive Introduction Strategy 

Let your middle management champions introduce you upward. They understand internal politics, timing, and how to frame solutions for executive consumption.

Message Script That Works

Here's the approach that generated those results:

Research Depth

• Individual: Recent posts, career progression, mentioned challenges

• Company: Recent news, competitor moves, industry headwinds

• Role-Specific: Department goals, typical pain points, decision criteria

Message Structure

• Personal connection: Recent post engagement or shared challenge

• Specific insight: Industry trend affecting their role

• Relevant example: How similar companies/roles benefit

• Soft ask: Exploratory conversation, not hard sales pitch

Follow-Up Strategy

• Value-add: Share relevant articles, insights, or tools

• Peer proof: Examples from similar roles at comparable companies

• Executive path: "Would this be worth discussing with your team?"

This strategy works across industries, especially for startups selling to large enterprises:

Financial Services: Target compliance managers before CFOs

Healthcare: Reach IT directors before CIOs

Manufacturing: Connect with operations managers before plant directors

Technology: Engage engineering managers before CTOs

The pattern holds: Find the people who feel your problem daily, then let them sell upward for you.

Middle-up selling creates advantages beyond just pipeline generation too.

Faster Implementation When end users are involved from the beginning, deployment goes smoother because they understand and want the solution.

Better Product Feedback Daily users provide more actionable feedback than executives who don't use the product directly.

Expansion Opportunities Champions at the operational level can identify additional use cases and departments that might benefit.

Stronger References Users who see daily value become your most credible references for similar prospects.

Why This Matters Now

Enterprise buying has become more committee-driven and risk-averse. Top-down selling assumes a decision-making structure that no longer exists at most large companies.

Middle-up selling acknowledges the reality of modern enterprise sales: Decisions bubble up from users who experience value, not down from executives who see budget line items.

For startups competing against established vendors, this approach levels the playing field. You might not have their brand recognition or enterprise sales teams, but you can build grassroots advocacy among the people who actually need your solution.

How I Can Help?

Let me book sales calls for you while you’re mapping your middle-up strategy. Seriously.

I built Valley to be your automated SDR and empower AEs. Get started today and watch your calendar fill up with qualified leads.

How can we work together 🏔️

1. See more of Valley’s messaging examples, feel free to roast them: https://joinvalley.notion.site/

2. Generate more demos for your company using LinkedIn: https://meetings.hubspot.com/zayd-from-valley/tryvalley
   

3. Become a Valley partner and get 20% recurring commission for every user you bring in: https://withvalley.notion.site/valley-affiliate-partner-program