Aspireship

Aspireship Inc operates multiple brands to help people transform their career trajectory.

Our brands:

Aspireship - Upskilling platform for B2B tech companies 
- aspireship.com

Orchard - Career Discovery for students and career changers
- orchard.careers

Teacher Career Coach - Online Courses, resources and community to help transitioning teachers find a great career after deciding to leave the classroom. 
- teachercareercoach.com

Founder & CEO

Story Ventures

As a Scout Investor, I'm privileged to be able to invest in founders of early-stage startups with the conviction to create positive change.

Story Ventures is an early stage VC fund based in NYC.

We invest in entrepreneurs with big visions that leverage technology and the proliferation of data to impact the way people interact with the world.

Scout Investor

MINDBODY, Inc.

Acquired by Vista Equity Partners.

Led the integration of Frederick into the MINDBODY organization. Frederick now powers the MINDBODY and Booker premium product editions to bring AI driven marketing to beauty, fitness and wellness businesses worldwide.

Vice President & GM, Frederick

Booker Software

Acquired by MINDBODY.

Continued to operate as CEO of Frederick following the acquisition by Booker Software.

CEO, Frederick

Frederick

Acquired by Booker and MINDBODY. 

Created the world’s first marketing automation platform for local businesses that’s powered by artificial intelligence. We call him Frederick, and he’s the smartest marketing engine local businesses have ever seen.

Dell

Building Dell's relationships with top venture capital firms, angel investors, Fortune 500 innovation departments and fast-growth startups.

Director, Center for Entrepreneurs

PhoneTell

PhoneTell makes mobile local search apps for consumers and wireless operators. 

My role was a hybrid of product management and business development. I was responsible for a Top 40 Travel & Local consumer app and worked alongside the CEO/COO to close and support deals with large wireless carriers globally.

VP, Product & Business Development

Game Change Ventures

Worked with consumer internet, e-commerce and SaaS startups to help them launch and grow innovative companies.

Managing Partner

Club E Network

Grew a local organization that began as a student club at Arizona State University into a multi-state organization with 10 chapters and an online network reaching entrepreneurs around the world.

President

The Business Journal

Guest Columnist

CEO @ Aspireship | Helping people get hired in tech sales and customer success

I’ve dedicated my professional career to helping people who want to help themselves. Currently, I’m building Aspireship Inc.

Aspireship Inc operates multiple brands to help people transform their career trajectory.

Our brands:

Aspireship - Upskilling platform for B2B tech companies 
- aspireship.com

Orchard - Career Discovery for students and career changers
- orchard.careers

Teacher Career Coach - Online Courses, resources and community to help transitioning teachers find a great career after deciding to leave the classroom. 
- teachercareercoach.com



Corey Kossack

Toast

Inside Sales Account Executive

🔬 The Practice Lab

Strategic Advisor

Modus

Work with Modus Commercial leaders to develop, train and coach demand generation competencies.  
Work with marketing and sales leadership to identify, train, monitor and improve KPI’s for outbound prospecting, inbound qualification, and overall demand generation performance.
Work with sales and marketing leadership to identify, train, monitor and improve key business competencies within the buyer’s journey that drive demand performance KPIs.
Work with sales and marketing leadership to identify and build the process, content, and technologies that enable all skills and competencies for AE, AM, and BDR functions. 
Provide a cadence of reporting on AE/BDR performance of outbound demand generation, inbound lead qualification, meeting quality, opportunity development and progression.

Head of Revenue Enablement 

Sales Enablement:
- Determine Sales Enablement priorities with sales stakeholders
- Work with sales leadership to develop, execute, optimize and assess Enablement program
- Communicate enablement strategy and KPIs to stakeholders
- Gather and relay feedback to continuously iterate on the Enablement strategy
- Use performance data to identify knowledge or skill gaps across the sales team
- Build a trusted relationship with sales reps
- Provide effective onboarding and training programs for sales reps (Process, Messaging, Systems)
- Coordinate educational content for ongoing training & Facilitate content creation with shared resources
- Maintain sales enablement software to ensure it is easily accessible and providing the capabilities sellers need 

Revenue Operations:
- Partner with Head of Sales to create, maintain and evolve Sales Process
- Serve as a liaison between sales, marketing and product teams
- QBR and Sales Meeting program management
- Partner with Sales and Marketing on GTM Strategy (Campaigns)
- Serve as program manager for any and all sales GTM programs

Revenue Operations and Enablement Lead 

Account Executive

KO Advantage Group

Chief Revenue Officer (CRO)

Sales Training & Business Development

Equinox

Exceeded yearly revenue goal of $8M+ ARR across 6 Equinox NY/CT locations 
Onboarded and led team of 15+ Membership Advisors to exceed KPIs in lead generation, follow-up activity, appointment setting, and closing
Delivered corporate sales training for 30-50 new hire employees at New York City global HQ monthly
Led company for 3+ years with lowest regional turnover (39%)  
Organized regional marketing and community outreach planning

Regional Sales Manager

Senior Membership Advisor

Membership Advisor

Revenue Enablement @ Modus | Sales Romantic | New Dad 😅

“We don't rise to the occasion. We fall to the level of our preparation." 🏆

“Don't wish it were easier. Wish you were better." 💪🏼

“Well begun is half done." 💯

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The Battle

Corey Kossack

Mike Macchiarelli

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