How Shepherd Started 56 Enterprise Conversations
How Shepherd Started 56 Enterprise Conversations
Enterprise outbound playbook: deliverability, tier-matched authority, and value-first messaging.
56
Enterprise leads
48,565
Contacts
Company
Enterprise-focused team starting sales conversations with billion-dollar companies.
Industry
Enterprise
Location
United States
Company
Enterprise-focused team starting sales conversations with billion-dollar companies.
Industry
Enterprise
Location
United States
Company
Enterprise-focused team starting sales conversations with billion-dollar companies.
Industry
Enterprise
Location
United States
At a glance
Enterprise outbound is harder: tougher inboxes, longer deals, and higher expectations. Shepherd used deliverability, authority, and hyper-specific messaging to open conversations with companies like Lionsgate and the San Diego Padres.
At a glance
Enterprise outbound is harder: tougher inboxes, longer deals, and higher expectations. Shepherd used deliverability, authority, and hyper-specific messaging to open conversations with companies like Lionsgate and the San Diego Padres.
At a glance
Enterprise outbound is harder: tougher inboxes, longer deals, and higher expectations. Shepherd used deliverability, authority, and hyper-specific messaging to open conversations with companies like Lionsgate and the San Diego Padres.
challenge
Start enterprise conversations without treating the market like a volume list
Enterprise outbound has a higher bar than mid-market or SMB outreach. Inbox placement is harder, deal sizes are larger, and buyers expect more evidence that the sender understands their world. A broad title filter or a generic pitch would create noise, not conversations.
Shepherd needed a playbook built for specific personas inside billion-dollar companies, with enough authority and relevance to make the first reply plausible.
challenge
Start enterprise conversations without treating the market like a volume list
Enterprise outbound has a higher bar than mid-market or SMB outreach. Inbox placement is harder, deal sizes are larger, and buyers expect more evidence that the sender understands their world. A broad title filter or a generic pitch would create noise, not conversations.
Shepherd needed a playbook built for specific personas inside billion-dollar companies, with enough authority and relevance to make the first reply plausible.
challenge
Start enterprise conversations without treating the market like a volume list
Enterprise outbound has a higher bar than mid-market or SMB outreach. Inbox placement is harder, deal sizes are larger, and buyers expect more evidence that the sender understands their world. A broad title filter or a generic pitch would create noise, not conversations.
Shepherd needed a playbook built for specific personas inside billion-dollar companies, with enough authority and relevance to make the first reply plausible.
Strategy
Build trust before asking for a sales conversation
Protect deliverability
For enterprise targeting, the inbox mix leaned toward Microsoft when appropriate, moving from the typical 50/50 Google and Microsoft split to as much as 70% Microsoft for larger businesses. DNS setup, a two-to-three-week warm-up period, and a slow ramp remained non-negotiable.
Establish tier-matched authority
The proof point had to match the prospect's level and industry. Rather than leading with a broad marketing-services message, the outreach framed a specialized problem and a specific value piece for the recipient's team.
Segment the exact persona
We avoided contacting an entire department. The approach focused on a small number of specific roles, then spoke to the specialized work those people owned. That made the outreach more relevant and protected the account relationship.
Use a value-first message and nurture the relationship
The aim of the first email was to start a conversation, not force a meeting. New leads were tracked in HubSpot through OutboundSync, with Fireflies, Make, and n8n supporting call-recording and proposal workflows as the relationship progressed.
Strategy
Build trust before asking for a sales conversation
Protect deliverability
For enterprise targeting, the inbox mix leaned toward Microsoft when appropriate, moving from the typical 50/50 Google and Microsoft split to as much as 70% Microsoft for larger businesses. DNS setup, a two-to-three-week warm-up period, and a slow ramp remained non-negotiable.
Establish tier-matched authority
The proof point had to match the prospect's level and industry. Rather than leading with a broad marketing-services message, the outreach framed a specialized problem and a specific value piece for the recipient's team.
Segment the exact persona
We avoided contacting an entire department. The approach focused on a small number of specific roles, then spoke to the specialized work those people owned. That made the outreach more relevant and protected the account relationship.
Use a value-first message and nurture the relationship
The aim of the first email was to start a conversation, not force a meeting. New leads were tracked in HubSpot through OutboundSync, with Fireflies, Make, and n8n supporting call-recording and proposal workflows as the relationship progressed.
Strategy
Build trust before asking for a sales conversation
Protect deliverability
For enterprise targeting, the inbox mix leaned toward Microsoft when appropriate, moving from the typical 50/50 Google and Microsoft split to as much as 70% Microsoft for larger businesses. DNS setup, a two-to-three-week warm-up period, and a slow ramp remained non-negotiable.
Establish tier-matched authority
The proof point had to match the prospect's level and industry. Rather than leading with a broad marketing-services message, the outreach framed a specialized problem and a specific value piece for the recipient's team.
Segment the exact persona
We avoided contacting an entire department. The approach focused on a small number of specific roles, then spoke to the specialized work those people owned. That made the outreach more relevant and protected the account relationship.
Use a value-first message and nurture the relationship
The aim of the first email was to start a conversation, not force a meeting. New leads were tracked in HubSpot through OutboundSync, with Fireflies, Make, and n8n supporting call-recording and proposal workflows as the relationship progressed.
Result
56 interested enterprise leads from 48,565 contacts
The campaign generated 56 interested leads from 48,565 contacts and opened sales conversations with prospects at companies including Lionsgate, the San Diego Padres, and ESL FACEIT Group.
The system was built for a longer enterprise sales process: deliverability first, then relevant authority, precise persona targeting, value-led messaging, and CRM-driven follow-up.
Result
56 interested enterprise leads from 48,565 contacts
The campaign generated 56 interested leads from 48,565 contacts and opened sales conversations with prospects at companies including Lionsgate, the San Diego Padres, and ESL FACEIT Group.
The system was built for a longer enterprise sales process: deliverability first, then relevant authority, precise persona targeting, value-led messaging, and CRM-driven follow-up.
Result
56 interested enterprise leads from 48,565 contacts
The campaign generated 56 interested leads from 48,565 contacts and opened sales conversations with prospects at companies including Lionsgate, the San Diego Padres, and ESL FACEIT Group.
The system was built for a longer enterprise sales process: deliverability first, then relevant authority, precise persona targeting, value-led messaging, and CRM-driven follow-up.
