Sales Engagement Cadence Specialist

Overview

You own the "Cadence Factory" at Hyland—building, testing, and optimizing the email sequences, call scripts, and social touches that SDRs and AEs use in Salesloft. You take strategic sales plays from marketing and leadership, turn them into executable cadences, then measure performance and iterate. You work cross-functionally with SDR leadership, field marketing, solution marketing, and ops to make sure outreach is consistent, on-message, and actually drives meetings.

Role Snapshot

Company Context

Stage: Private, mature (4,100+ employees, decades in business)

Size: 4,143 employees

Growth: Established player in content services/ECM with enterprise customers across healthcare, government, insurance, financial services, higher education

Market Position: Leader in ECM space, competing with legacy players and newer cloud-native solutions. Known for deep vertical expertise but selling complex, technical software that requires long sales cycles.

GTM Reality

Pipeline Sources:

• Likely 30-40% inbound from existing customer base, industry events, and website traffic (mature company with brand recognition)
• 60-70% outbound—cold calling and email to target accounts in key verticals
• Some partner/channel motion given enterprise focus

SDR/AE Structure: Dedicated SDR team feeding AEs. You're supporting both—SDRs running cadences for net-new outbound, AEs running cadences for direct account work and following up on SDR-generated opps.

SE Support: Yes, SEs support technical demos and POCs for complex enterprise deals.

Competitive Landscape

Main Competitors: Likely competing with Microsoft (SharePoint), OpenText, Box, newer players like DocuSign/Docusign CLM, vertical-specific ECM solutions

How They Differentiate: Deep vertical expertise (healthcare compliance, government records management), mature product with extensive integrations, strong services/support org

Common Objections: "We already use SharePoint," "Too expensive," "Implementation timeline too long," "We're going with a cloud-native solution"

Win Themes: Vertical-specific functionality, compliance/security features, proven track record with similar customers, integration ecosystem

What You'll Actually Do

Time Breakdown

Cadence Building (30%) | Performance Analysis (25%) | Cross-functional Collaboration (25%) | Testing/Iteration (20%)

Key Activities

• Building Cadences in Salesloft: You take a strategic play ("We're targeting CFOs at mid-market healthcare systems with our AP automation story") and turn it into a 10-touch sequence—4 emails, 4 calls, 2 LinkedIn touches. You write copy, set timing, coordinate with marketing on assets to attach.

• Analyzing Performance: You pull reports on open rates, reply rates, meeting-booked rates by cadence, persona, vertical. You figure out which subject lines work, which call-to-actions get responses, which touches get ignored. You present findings to SDR leadership and make recommendations.

• Cross-functional Coordination: You sit in meetings with field marketing (who wants to promote a webinar), solution marketing (who has new messaging), SDR managers (who say reps aren't using a cadence), and ops (who wants to add another field to track). You translate strategic priorities into execution plans.

• Standardizing Execution: You train SDRs and AEs on new cadences, create documentation, enforce best practices. You're the quality control—making sure a rep in Boston is sending the same message as a rep in Dallas when targeting the same persona.

The Honest Reality

What's Hard

• Balancing volume and customization: Leadership wants scale and consistency, but reps want flexibility to personalize. You're constantly negotiating what's templated vs. what's customizable, and enforcing it in Salesloft.

• Measuring true impact is fuzzy: You can track open rates and replies, but connecting a specific cadence change to pipeline created 6 months later is hard. You'll spend time justifying your work and fighting for resources.

• Everyone has an opinion on messaging: Marketing thinks their copy is perfect, SDR managers say it doesn't resonate, AEs ignore it entirely and write their own. You're herding cats to get alignment, and someone's always unhappy with the compromise.

• Reps don't always follow the playbook: You build a great cadence, roll it out, then find out half the team isn't using it or is skipping steps. Adoption is a constant battle.

What Success Looks Like

• Your cadences have 15-20% reply rates (good for cold outbound in enterprise software) and consistently book 10-15% of touches into meetings
• SDR and AE teams actually use your cadences instead of doing their own thing—80%+ adoption rates
• You can point to specific cadence changes that improved meeting-booked rates by X% in a target segment
• Leadership asks you to build cadences for new GTM plays because your stuff works

Who You're Selling To

You're not selling—you're enabling the teams who sell to:

Primary Buyers (for Hyland's software):

• VP/Director of IT Operations at healthcare systems, government agencies, insurance companies
• CIOs, CTOs evaluating enterprise content management platforms
• Compliance officers, records managers in regulated industries

What They Care About:

• Compliance and security (HIPAA, government records retention, etc.)
• Integration with existing systems (EHR systems in healthcare, core banking systems, etc.)
• Reducing paper-based processes and manual workflows
• Vendor stability and long-term support (they're buying enterprise software for 5-10 year deployments)

Requirements

• 2-4 years in sales enablement, sales ops, or SDR/BDR leadership roles—you've done the job or managed people doing it
• Deep experience with Salesloft or similar engagement platforms (Outreach, Apollo)—you know how to build multi-channel cadences, A/B test, and pull performance reports
• Strong copywriting skills—you can write compelling cold emails and call scripts that sound like a human, not a robot
• Data-driven mindset—you pull reports, analyze metrics, and make decisions based on numbers, not hunches
• Cross-functional collaboration—you can work with marketing (who speaks in campaigns), SDR managers (who care about activity metrics), and ops (who want clean data) without losing your mind
• B2B enterprise software experience preferred—understanding long sales cycles, complex buyer committees, and vertical-specific messaging
• Comfortable with ambiguity—this role is part strategy, part execution, part politics. You figure it out as you go.