Cold calling C-suite executives remains one of the most challenging yet rewarding aspects of B2B sales prospecting. The path to decision-makers is often blocked by skilled executive assistants and personal assistants who excel at gatekeeping. According to recent sales data from over 20 million calls analyzed by Koncert, reaching C-level prospects requires strategic timing, personalized messaging, and respect for the gatekeeper's role.
This comprehensive guide reveals proven techniques for breaking through to CEOs, CFOs, CMOs, and other senior executives, based on real-world insights from the Cold Calling in 2025: Koncert & Seamless.AI webinar and data from sales professionals who consistently connect with top-tier decision-makers.
Executive assistants aren't obstacles—they're highly trained professionals protecting their executive's time from irrelevant interruptions. The average CEO receives 200+ outbound sales calls monthly, making gatekeepers essential filters for executive productivity.
The EA's Primary Responsibilities:
Screening low-value sales pitches
Managing executive calendars strategically
Prioritizing genuinely important calls
Protecting decision-maker focus time
Successful C-suite cold calling starts with respecting the PA's position. They're not adversaries—they're potential allies who can accelerate your sales pipeline if approached correctly. Executive assistants often influence purchasing decisions and can become internal champions when they recognize genuine value.
Sales professionals report significantly higher connect rates when calling C-suite executives between 7:00-8:00 AM. During these early hours, executives are typically:
Arriving before their assistant starts work
Reviewing priorities before meetings begin
More receptive to focused conversations
Less overwhelmed by daily fire drills
Why Early Morning Works: According to insights from the Koncert webinar, early mornings (7-8 AM) work more effectively because recipients haven't usually started their day yet. Executives answer their own phones during this window, bypassing gatekeeper screening entirely.
Different industries operate on varying schedules, requiring adaptive cold calling strategies:
Construction & Manufacturing:
Best time: 7:30 AM - 8:30 AM
Rationale: Executives arrive early before job sites activate
Decision-makers are in-office before operational chaos begins
Technology & Professional Services:
Best time: 8:00 AM - 9:00 AM or 4:30 PM - 5:30 PM
Rationale: Before standard business hours or after assistant departures
Restaurant & Hospitality:
Best time: 2:00 PM - 4:00 PM
Rationale: Between lunch and dinner service
Executives avoid late mornings when they're still off-site
Healthcare & Medical:
Best time: 7:00 AM - 8:00 AM
Rationale: Before patient schedules begin
The 4:30-6:00 PM window offers another strategic cold calling opportunity. Executive assistants typically leave by 5:30 PM, while senior leaders often work later. During this timeframe, C-suite prospects answer their own phones and may be more conversational after completing daily priorities.
Friday calling generates mixed results for C-suite prospecting. While some sales data suggest improved pickup rates, meeting quality and show-up rates require consideration. Webinar participants noted that Friday afternoons can work in your favor for casual conversations as prospects are typically more relaxed, but serious business discussions may be better scheduled earlier in the week.
The day before holidays present exceptional opportunities executives are typically more relaxed and receptive, like Friday energy but with even better disposition.
When the EA answers, honesty combined with value clarity works effectively:
Effective Script: "Good morning, this is [Your Name] from [Company]. I'm calling to speak with [Executive Name] about [specific value proposition relevant to their role]. Is this a good time to connect, or would you recommend I call back at a better time?"
Why This Works:
Shows respect for the assistant's time
Demonstrates you're not hiding your intent
Frames the call around executive priorities
Positions the EA as a helpful advisor
Position yourself as another professional, not a vendor:
"Hi, I'm [Name], I work with [Executive Name]'s peers at [Similar Company] on [specific initiative]. I wanted to share some insights that might be relevant. Could you let me know the best way to reach them?"
Key Elements:
Establishes credibility through peer association
Focuses on sharing insights, not selling
Respects the screening process
Creates curiosity about peer activities
Demonstrate you've done homework before calling:
"Good afternoon, I noticed [Executive Name] recently [LinkedIn post/company announcement/interview quote]. I work with other [role titles] on [related initiative] and thought this might be timely. Would [Executive Name] be available for a brief conversation?"
Power of Personalization:
Proves this isn't a generic cold call
Shows genuine interest in their business
Creates relevance through current events
Increases gatekeeper's willingness to connect
Referenced connections dramatically improve gatekeeper navigation:
"Hi, [Mutual Connection] suggested I reach out to [Executive Name] regarding [specific topic]. Is this a good time to connect briefly?"
Even without direct referrals, industry associations and shared interests create soft connections that reduce resistance.
For particularly difficult gatekeepers, multiple touchpoints create familiarity:
6-8 Call Sequence Before First Voicemail: Some sales professionals recommend calling 6-8 times without leaving voicemail initially. This strategy:
Creates caller ID recognition
Avoids the "voicemail black hole"
Increases curiosity about persistent caller
Eventually prompts the EA to ask who's calling
Alternative: First Call Voicemail: Others advocate leaving voicemail on the first attempt using the prospect's name to establish legitimacy and differentiate from spam.
Position your call as helpful for the assistant:
"I wanted to make sure I'm reaching out during a time that works best for [Executive's] schedule. Based on your experience, when do they typically have a few minutes for exploratory conversations with [your industry/solution]?"
Benefits:
Positions EA as the expert
Shows respect for their schedule management
Creates collaborative dynamic
Often results in inside information about best contact times
Calling executive cell phones offers several benefits:
Direct access without gatekeeper screening
Higher likelihood of reaching decision-makers
IT and field executives prefer mobile contact
More personal connection opportunity
When C-suite prospects express annoyance about cell phone calls:
Effective Apology Approach: A simple apology for the cell dial can help overcome objections for the call.
Effective Response: "[Executive Name], I apologize for calling your mobile directly. I wanted to ensure this reached you personally given [time-sensitive value proposition]. Do you have 60 seconds for me to explain why I called it?"
When to Use Office Lines
Office numbers remain appropriate for:
Initial outreach to unfamiliar prospects
Industries with strong gatekeeper relationships
Executives who publicly share office contact information
Government and highly regulated sectors
Platform Tip: Koncert's AI Parallel Dialer automatically manages local presence caller IDs, increasing pickup rates by matching your outbound number to the prospect's area code making executives more likely to answer thinking it's a local, potentially important call.
Sales experts emphasize that getting past the first three seconds is where cold calling becomes an art. C-suite executives decide whether to continue conversations almost instantly.
Framework #1: The Problem-Agitation Opener
"[Executive Name], companies like yours in [industry] are dealing with [specific challenge]. I work with [similar companies/competitors] to [specific outcome]. Is this something on your radar?
Framework #2: The Insight-Sharing Approach
"[Executive Name], I've been researching [their company] and noticed [specific observation about their business/market]. We've helped similar organizations [achieve specific result]. Worth a brief conversation?"
Framework #3: The Direct Value Statement
"[Executive Name], we help [ICPs] avoid/reduce/eliminate [specific pain point]. Can I ask you three quick questions to see if this might be relevant?
The Three-Question Method: When executives show interest, engage them with qualifying questions:
"How significant is [problem] for your organization?"
"How frequently does [issue] occur?"
"What's currently causing [the challenge]?"
This framework flips the script, making the executive engage rather than dismiss. One webinar participant noted that progressing to these questions often indicates genuine interest and emphasized the importance of multi-stakeholder meetings rather than one-on-one conversations to ensure follow-through.
"How are you today?" (Too casual/scripted)
"Did I catch you at a bad time?" (Invites immediate no)
"I'm following up on my email..." (They deleted it)
"I was just wondering if..." (Sounds uncertain)
"Do you have a few minutes?" (Too vague)
Creating targeted lists of prospects based on ideal customer profiles, firmographics, and technographics. The quality of your sales prospecting lists directly impacts your pipeline's health.
Instead, Be Direct: C-suite executives appreciate brevity and clarity. Webinar participants emphasized that when receiving sales calls themselves, they prefer when salespeople get straight to the point about what they want.
Multiple sales professionals report better results combining LinkedIn outreach with phone calls:
Proven Sequence:
Day 1: Send personalized LinkedIn connection request mentioning specific mutual interest or company observation
Day 2: Once connected, send brief message with value proposition
Day 3: Phone call referencing LinkedIn interaction
Why This Works:
Creates familiarity before the call
Demonstrates genuine interest through research
Provides social proof via LinkedIn profile
Reduces "stranger danger" factor
Gives gatekeepers context ("They're already connected on LinkedIn")
Effective Pattern
Day 1: Send high-value email with specific insight or resource
Day 2: Follow-up call: "I sent over some information about [topic] yesterday. Did you have a chance to review it?"
Cross-Channel Strategy: One effective approach shared in the webinar involves leaving a voicemail that points prospects to an email sent immediately after the call. This cross-channel approach creates multiple touchpoints while demonstrating organization and follow-through.
Optimized Voicemail Strategy:
Keep under 30 seconds (industry best practice)
Use prospect's name (builds legitimacy)
State specific value proposition
Reference follow-up email
Provide direct callback number
Value-Focused Voicemails:Focus entirely on prospect benefit, not your product features. Webinar insights suggest leaving short voicemails that clearly communicate what's in it for the prospect.
Prevention Strategy: Don't give prospects the opportunity to make that statement. There are strategic techniques to steer the conversation away from that immediate dismissal response.
If They Say It Anyway: I completely understand, [Executive Name]. Most executives I work with said the same thing initially—until they learned about [specific unexpected benefit]. Can I share one quick example that might change your perspective?
Smart Response: I'd be happy to send over relevant materials. To make sure I send exactly what would be most valuable, can I ask: What specifically about [topic] is most important to your organization right now?
This qualifies their interest while gathering intelligence for targeted follow-up.
Effective Counter: That's great you're already prioritizing [area]. Most of our clients also worked with [competitor type] before switching to our approach because of [unique differentiator]. Would you be open to a brief comparison of conversation to ensure you're getting the best possible [outcome]?
Strategic Response: I appreciate you being upfront about timing. Many executives say the same thing; then later wish they'd started the conversation earlier. Can I ask what would need to change for this to become a current priority?
This uncovers the real objection while demonstrating you understand executive decision-making timelines.
Modern sales teams use advanced dialing technology to increase C-suite contact rates:
Koncert's AI Parallel Dialer Benefits:
150-200+ calls per hour dramatically increases chances of reaching busy executives
Ultra-low latency connects ensure you're in the conversation instantly when they answer
Local presence caller IDs automatically match executive's area code for higher pickup rates
Caller ID health management prevents your number from being flagged as spam
Quick Connect technology eliminates awkward lag that causes hang-ups
Connect Rate Data: Industry benchmarks show 5-15% connect rates depending on list quality and targeting. With optimized outbound calling strategies, top performers achieve 15%+ connection rates with C-suite prospects.
Real-Time Coaching Benefits:
Managers listen to live calls
Whisper mode provides guidance without prospect hearing
Identify what's working/failing immediately
Improve talk tracks based on actual executive responses
Conversation Intelligence Features:
AI identifies common objections
Transcript analysis reveals successful patterns
Build call library of winning executive conversations
Train entire team on proven approaches
AI PitchLab for Practice: Koncert's AI PitchLab allows reps to practice conversations with AI personas mimicking skeptical executives. This safe environment builds confidence before real executive calls.
Waterfall Data Enrichment Advantages:
Instantly verify direct dials
Eliminate wasted calls to bad numbers
Access multiple data sources automatically
Keep contact information current
Poor data quality wastes precious selling time. Webinar participants noted that data quality is critical, and even premium data sources can have inaccuracies. Using automated enrichment ensures you're calling verified executive numbers.
The best cold callers build ongoing relationships with executive assistants:
Relationship-Building Tactics:
Remember and use the EA's name consistently
Ask about their recommendations on timing
Thank them for their help
Update them on conversation outcomes
Send occasional thank-you notes
Why This Matters: Executive assistants talk to each other. A good reputation with one EA can open doors across an entire industry or market segment.
Some personal assistants are trained to be extremely protective:
Stay Professional:
Never argue or show frustration
Avoid manipulation tactics
Don't try to deceive the assistant
Respect firm boundaries
Alternative Approaches:
Try different calling times when EA may not be present
Use LinkedIn InMail to bypass phone screening
Attend industry events where executives are accessible
Leverage referrals and mutual connections
Essential Metrics:
Connect rate: Percentage of calls reaching decision-maker
Conversation length: Average talk time with executives
Meeting booking rate: Successful appointments set
Pipeline contribution: Revenue attributed to conversations
Time to connect: Number of attempts before reaching executive
While volume matters for broader prospecting, calling requires quality focus:
70-100 Calls Daily Benchmark: Industry data from the Koncert and Seamless.AI webinar suggests 70 calls per day as minimum for pipeline building, with 100+ being optimal. However, for C-suite targeting specifically, 30-50 highly researched, perfectly timed calls often outperform 100+ generic attempts.
Test Variables:
Early morning vs. end of day calling
Direct mobile vs. office line outreach
Different opening lines and value propositions
Voicemail on first call vs. multiple attempts first
LinkedIn warm-up vs. cold call first
Track these variables systematically to identify what works best for your specific C-suite audience.
Characteristics:
Highly protective of time
Respond well to data and metrics
Appreciate technical credibility
Often early adopters
Approach: Lead with specific metrics, case studies from recognizable tech companies, and technical differentiation. CTOs and CIOs value efficiency—get to the point quickly.
Characteristics:
Patient outcome focused
Complex stakeholder environment
Regulatory constraints
Long sales cycles
Approach: Frame conversations around patient experience, clinical outcomes, and operational efficiency. Understand healthcare acronyms and demonstrate industry knowledge.
Characteristics:
Risk-averse decision-making
Require compliance awareness
Value ROI discussions
Prefer conservative communication
Approach: Emphasize security, compliance, and quantifiable returns. Reference to regulatory knowledge and include risk mitigation in your value proposition.
Characteristics:
Operations-oriented thinking
Focus on efficiency and uptime
Practical, hands-on perspective
Value proven solutions
Approach: Emphasize operational improvements, downtime reduction, and tangible efficiency gains. Manufacturing executives appreciate concrete examples over theoretical benefits.
Strategy: Instead of a "sales call," position the conversation as an executive briefing:
"[Executive Name], I've prepared a brief 10-minute executive briefing on how [peer companies] are addressing [industry challenge]. Would [Day/Time] work to walk you through the key findings?"
Why This Works:
Positions you as a thought leader, not a vendor
Appeals to executive desire for competitive intelligence
Creates structured, time-bound commitment
Demonstrates preparation and professionalism
Multi-Threading Strategy: Rather than targeting only the CEO or primary decision-maker:
Why This Works:
Research the full C-suite team
Identify 3-4 relevant executives
Develop personalized value propositions for each role
Connect with multiple executives over 2-3 weeks
Benefits:
Creates internal conversations about your solution
Reduces dependency on single gatekeeper
Demonstrates enterprise-level thinking
Increases chances of finding a champion
Comprehensive Approach: Combine calling with broader account research:
Call C-suite during optimal windows
Connect with director/VP level during standard hours
Build relationships with multiple stakeholders
Create internal momentum toward engagement
This multi-level approach often results in introductions upward to C-suite from lower-level champions.
C-suite executives hear dozens of generic pitches weekly. Avoid:
We help companies save time and money
We're the leading provider of...
I wanted to see if you'd be interested in...
The 80/20 rule applies especially to C-suite conversations. Sales reps should listen to 80% and talk 20%. Executives want to discuss their challenges, not hear product monologues.
Treating executive assistants as obstacles rather than professionals damages your reputation and eliminates any chance of reaching the decision-maker.
Calling repeatedly at the same unsuccessful time demonstrates a lack of strategic thinking. If 2:00 PM doesn't work after three attempts, try early morning or end of day.
C-suite executives expect you to know:
Their company's recent news and initiatives
Industry trends affecting their business
Competitive landscape
Your specific value proposition for their situation
This opener invites immediate "yes" and calls for termination. Instead, acknowledge time constraints while demonstrating value:
"I know you're incredibly busy, [Executive Name]. I'll be brief and specific about why I called..."
Fumbling through research during the call wastes their time and ends the conversation quickly.
How many times should I try calling a C-suite executive before giving up?
Best practice suggests 8-12 attempts across different times and days. Sales professionals note that persistence pays off with executives but vary your calling times. Try early mornings (7-8 AM), mid-afternoons, and end-of-day (4:30-5:30 PM) across multiple weeks.
Should I leave a voicemail on the first call to a C-suite executive?
Opinions differ among sales professionals. Some recommend 6-8 calls before leaving your first voicemail to avoid the "voicemail black hole." Others advocate leaving a brief, value-focused voicemail immediately to establish legitimacy. According to insights from the Cold Calling in 2025 webinar, using the prospect's name and dropping your name helps ensure you aren't mistaken for spam. Test both approaches to see what works for your industry.
How do I handle an executive assistant who refuses to connect me?
Respect their decision, thank them professionally, and try alternative strategies: call during non-EA hours (early morning/late day), connect via LinkedIn, attend industry events, or seek referrals from mutual connections. Never argue with or attempt to deceive gatekeepers.
What's the ideal length for a C-suite cold call conversation?
Keep initial conversations for under 5 minutes. Respect executive time by being concise and value-focused. The goal is qualifying interest and scheduling a proper meeting, not conducting a full needs analysis on the first call.
Should I use mobile or office numbers when calling C-suite?
Both have advantages. Mobile numbers bypass gatekeepers but may feel intrusive. Office numbers show professionalism but face screening. Test both, and if calling a mobile, acknowledge it immediately: "I apologize for calling your mobile directly..."
How do I research C-suite executives effectively before calling?
Review their LinkedIn profile, recent company announcements, earnings calls, industry interviews, social media posts, and company news. Spend 10-15 minutes per executive to understand their priorities, challenges, and communication style.
What's the best way to handle "Send me some information" from a C-suite prospect?
Respond with: "I'd be happy to send relevant materials. To ensure I send exactly what would be valuable—what specifically about [topic] is most important to your team right now?" This qualifies interest while gathering intelligence for targeted follow-up.
How can technology improve my C-suite connect rates?
Use AI-powered dialing platforms like Koncert that offer local presence caller IDs (automatically matching executive's area code), caller ID health monitoring (preventing spam flags), and ultra-low latency connects (eliminating awkward lag when they answer). These features dramatically improve pickup and conversation quality. Additionally, features like AI PitchLab help reps practice executive conversations before making real calls, and Waterfall Data Enrichment ensures you're calling accurate, verified numbers.
What if the executive gets annoyed that I'm calling their cell phone?
Acknowledge it immediately with a simple apology: "[Executive Name], I apologize for calling your mobile directly. I wanted to ensure this reached you personally given [specific value proposition]. Do you have 60 seconds?" Most executives appreciate the direct acknowledgment.
How do I know if I'm calling C-suite prospects at the right time?
Track your data. Monitor connect rates by time of day and day of week. Industry matters—construction executives start early (7:30 AM), while restaurant executives are available mid-afternoon (2-4 PM). According to data from the Koncert cold calling webinar analyzing over 20 million calls, timing patterns emerge based on industry, role, and geography. Test different windows and optimize based on your results. Use analytics dashboards to track performance and identify optimal calling windows.
Breaking through to C-suite executives requires strategic thinking, impeccable timing, and genuine value delivery. Success comes from respecting both the gatekeeper's role and the executive's time while demonstrating clear relevance to their business priorities.
Key Takeaways:
Call early mornings (7-8 AM) when executives answer their own phones
Build relationships with executive assistants rather than viewing them as obstacles
Research thoroughly before every call to demonstrate genuine interest
Lead with specific value propositions relevant to the executive's role
Use technology like Koncert's AI dialing platform to optimize timing, manage caller ID health, and connect quickly
Practice your pitch using AI training tools before high-stakes executive calls
Track your metrics and continuously refine your approach
The sales professionals who consistently reach C-suite decision-makers share common traits: persistence without annoyance, preparation without over-scripting, and confidence without arrogance. They understand that every executive conversation is an opportunity to add value, not just close a deal.
By implementing the strategies outlined in this guide from optimal timing windows to gatekeeper navigation techniques to value-based messaging you'll dramatically improve your C-suite connect rates and build a robust pipeline of high-value opportunities.
Remember: C-suite cold calling isn't about tricks or manipulation. It's about demonstrating that your solution deserves their attention and that you respect their time enough to be thoroughly prepared when you finally connect.
Start implementing these strategies today, measure your results with robust analytics tools, and continuously refine your approach. The path to C-suite conversations is challenging but entirely achievable with the right strategy, tools, and mindset.
Ready to improve your C-suite connect rates? Koncert's AI-powered dialing platform helps sales teams reach more executives with features like automated local presence, caller ID health monitoring, and ultra-low latency connects. Learn more about how Koncert can accelerate your executive outreach by exploring our solutions for different business segments.
Want to dive deeper into cold calling best practices? Watch the full Cold Calling in 2025: Koncert & Seamless.AI webinar for data-driven insights from over 20 million calls.