How to Find and Connect with Hiring Managers: The Direct Outreach Strategy That Works

Most executives waste months applying to job postings through company websites and job boards. They submit carefully crafted applications into digital black holes, wait weeks for responses that never come, and watch their confidence erode with each ignored submission.

There's a better approach that experienced recruiters and career coaches have known for years: find the hiring manager directly and reach out before the formal application process even begins.

This strategy puts you in front of decision-makers while other candidates are stuck navigating applicant tracking systems. It transforms you from "resume #147 in the pile" to "that impressive executive who reached out with relevant experience."

Here's the complete framework for finding and connecting with hiring managers who can actually hire you.

Why Direct Outreach Works (And Applications Don't)

The traditional job application process is broken at the executive level. When you apply through a job posting, here's what actually happens:

Your resume enters an applicant tracking system alongside 200-500 other applications for the same role. The ATS scans for keyword matches based on the job description. If your resume doesn't contain the exact phrases the system is programmed to find, you're automatically filtered out—regardless of your qualifications.

Recruiters screen based on narrow criteria they've been given by hiring managers. They're looking for specific titles, company names, or industry experience. Any deviation from the perfect candidate profile reduces your chances significantly.

You have no relationship with anyone involved in the hiring decision. You're just a document in a system, competing with hundreds of other documents.

The timeline is glacial—typically 2-4 weeks before you might hear anything, and often you never hear back at all.

Now compare that to direct outreach to the hiring manager:

You're in their LinkedIn inbox within 24 hours of sending your message. They see your name, your current title, and a brief message explaining why you're reaching out.

You're a real person, not resume #147. You've demonstrated initiative by finding them directly. You've shown you can navigate business relationships and take action without waiting for formal processes.

You can explain your value in context rather than hoping a resume communicates it. You can reference their company's specific challenges, recent news, or strategic direction in ways that resonate.

The timeline compresses dramatically—you'll typically get a response within 48-72 hours if they're interested, or you'll know quickly that it's not the right fit.

The conversion rate difference is stark: direct outreach to decision-makers generates responses 10-20x more frequently than applications through job postings.

How to Find the Hiring Manager (Step-by-Step)

Finding the right person to contact requires strategic research, but it's simpler than most executives think.

Step 1: Identify Your Target Companies

Start by creating a list of 30-50 companies you'd genuinely want to work for. Don't just list every company in your industry. Be selective based on:

Company size and growth stage that matches your experience
Culture indicators from Glassdoor, news coverage, and employee LinkedIn posts
Strategic direction that aligns with your expertise
Location or remote work policies that fit your life
Compensation levels that meet your requirements

This target list becomes your prospecting universe for the next 8-12 weeks.

Step 2: Use LinkedIn to Find the Hiring Manager

LinkedIn is your primary research tool for identifying decision-makers. Use the search function with this formula:

"[Company Name] [Function] [Level]"

Specific examples:

"Stripe VP Engineering"
"Databricks Director Product Marketing"
"Figma Head of Sales Operations"
"Notion Chief Revenue Officer"

This search surfaces people with those titles at those companies.

Step 3: Look for the Right Level

The key is identifying who would actually make the hiring decision for your target role.

If you're targeting VP roles, you want to connect with:

SVP or C-level executives who would be your direct manager
Current VPs in similar functions who could be peers or hiring managers for the team
Recruiting leaders for that specific function (VPs of Talent Acquisition often partner directly with hiring managers)

If you're targeting Director roles, look for:

VPs or SVPs in that function
Senior Directors who might be building teams
Heads of specific departments

The hiring manager is typically one level above the role you're targeting.

Step 4: Verify They're the Decision-Maker

Before reaching out, spend 5 minutes reviewing their LinkedIn profile to confirm they're the right contact:

Check their current role description. Do they manage a team in the function you're targeting? Look for language like "building," "leading," or "overseeing" teams.

Review their recent posts. Have they mentioned hiring, team growth, or expanding their organization? This confirms they're actively building and signals they might be receptive to outreach.

Look at their connections. Do they have recruiters, talent acquisition partners, or team members in their network? This indicates they're involved in hiring decisions.

Check for team members reporting to them. If you can see their direct reports (many executives showcase their teams), you can confirm they manage the function you're targeting.

How to Reach Out (The Message Template That Works)

Once you've identified the hiring manager, you need a message that gets opened, read, and generates a response.

The key principles:

Keep it short (under 75 words)
Be specific about why you're reaching out
Demonstrate knowledge of their business
Lead with value, not need

Here's the proven template:

Subject: [Specific achievement] background for [Company Name]

Hi [Name],

I've been following [Company]'s growth in [specific space] and I'm impressed by [specific recent development, funding round, product launch, or strategic move].

I'm a [Your Role] with [X years] experience in [specialty]. I've [specific relevant achievement with quantified result]. I'm exploring opportunities in [function] and would love to connect about what you're building.

Are you open to a brief conversation?

[Your Name]

Example 1:

Subject: B2B SaaS scaling experience for Notion

Hi David,

I've been following Notion's evolution from productivity tool to platform and I'm impressed by your recent enterprise push.

I'm a VP of Sales with 12 years scaling B2B SaaS from $5M to $50M+ ARR. I've built enterprise sales functions from scratch at two companies, resulting in $80M+ in new revenue. I'm exploring opportunities in revenue leadership and would love to connect about what you're building.

Are you open to a brief conversation?

[Your Name]

Example 2:

Subject: Product-led growth experience for Figma

Hi Maya,

I've been following Figma's expansion beyond design into the broader product development stack—exciting direction.

I'm a VP of Product with 10 years in PLG companies. I've launched 6 products that generated $40M ARR and achieved viral growth coefficients above 1.4. I'm exploring product leadership opportunities and would love to connect.

Are you open to a brief conversation?

[Your Name]

Note what these messages include:

A specific observation about their business (not generic "I admire your company")
Your relevant title and experience level
A quantified achievement that demonstrates value
A clear, simple ask (just a conversation)

Note what they don't include:

Lengthy background stories
Desperation signals
Requests to "pick your brain" or vague networking language
Immediate asks about open positions

The Three Mistakes That Kill Response Rates

Most executives sabotage their outreach with these common errors:

Mistake 1: Generic Messages

"I'm reaching out about opportunities at your company" gets ignored every time.

Why? Because it tells the hiring manager nothing about:

Why you're specifically interested in their company
What value you might bring
Whether you understand their business
If you're worth 15 minutes of their time

Generic messages signal that you're mass-sending the same note to dozens of companies—which you might be, but they shouldn't feel like just another name on your list.

Mistake 2: Asking for a Job Immediately

"Are you hiring?" or "I'd like to apply for your VP of Marketing role" is too direct for initial outreach.

This approach:

Puts them on the spot to either say yes or reject you
Assumes there's an open role (there often isn't, but they might create one for the right person)
Positions you as "job seeker" rather than "potential high-value hire"

The better approach is asking for a conversation to explore fit—this leaves room for multiple outcomes beyond yes/no on a specific posted role.

Mistake 3: Long Messages

Messages over 100 words rarely get read by busy executives.

They're scanning their LinkedIn inbox between meetings, on their phone, or late at night. A long message signals:

You don't value their time
You can't communicate concisely
You're probably desperate (why else would you write so much?)

Keep your initial outreach to 50-75 words maximum. You can expand in follow-up if they respond.

What Happens When They Respond

When a hiring manager responds to your outreach, you want to schedule a brief 15-20 minute exploratory call (not a formal interview—yet).

On this call, your goals are to:

1. Learn about their current challenges - What's keeping them up at night? What problems is their team trying to solve? Where are the gaps?

2. Share relevant experience - When they describe challenges, reference specific situations where you've solved similar problems. Be brief and focus on outcomes.

3. Explore potential fit - Is there mutual interest in working together? Do your skills align with their needs? Is the timing right?

If there's genuine mutual interest, several outcomes are possible:

They introduce you to their recruiter (with their endorsement, which dramatically improves your odds)

They create a role for you (this happens more often than you'd think at the executive level—companies create positions for exceptional talent)

They keep you warm for future openings (and reach out when the timing is better)

They refer you to another executive in their network who has a more immediate need

All of these outcomes are substantially better than submitting a cold application through a job posting.

The Numbers Game: Making Direct Outreach Work

Direct outreach is effective, but it requires consistent volume and realistic expectations.

Here's what the math typically looks like:

Send 10-15 targeted messages per week to hiring managers at companies on your target list.

Expect a 20-30% response rate if your messages are well-crafted and relevant. That means 2-4 responses per week.

Expect 5-10% to turn into actual conversations beyond a brief reply. That means 1-2 real exploratory calls per week.

Do this consistently for 8-12 weeks and you'll build a strong pipeline of opportunities at various stages:

15-20 initial conversations
5-8 opportunities advancing to formal interviews
2-3 final-stage discussions
1-2 offers

This is dramatically more effective than submitting 50-100 applications through job postings, which typically generates 1-3 responses total.

Advanced Tactics: Following Up and Staying Visible

Most hiring managers won't respond to your first message—not because they're not interested, but because they're busy.

Your follow-up strategy should include:

First follow-up (7 days later): Add value with a relevant article, insight, or resource related to their business challenges.

Second follow-up (14 days later): Brief check-in referencing your previous messages and reiterating your interest.

Third follow-up (21 days later): Final message closing the loop and offering to reconnect in the future if timing improves.

After three attempts with no response, move on to other prospects on your target list.

The Direct Outreach Advantage

The executives who land the best roles aren't necessarily the most qualified—they're the ones who understand that hiring happens through relationships, not applications.

By finding and connecting with hiring managers directly, you:

Skip the broken ATS process entirely
Position yourself as a proactive problem-solver
Create conversations before formal job openings exist
Build relationships that lead to opportunities beyond posted roles
Demonstrate the initiative and business acumen that executives should have

This approach requires more research and personalization than mass-applying to job postings, but the return on your time investment is 10-20x higher.

Start building your target company list today, identify the hiring managers, and send your first messages this week. The opportunities won't come to you—you need to create them.

Ready to Accelerate Your Executive Job Search?

Finding and connecting with hiring managers is just one component of a complete executive job search system. If you want help developing a personalized strategy that generates multiple offers within 90 days, I can help.

Book a Strategy Call to discuss your specific situation and how to position yourself for the roles you want.

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