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

Alyson Baber Coaching

Founder

Stage 2 Capital

Limited Partner

Pavilion

Executive Member

Outreach

Responsible for 50% of the company revenue and 80% of the customers at Outreach

Led segments across US and Mexico in new client Acquisition, Growth and Expansion, and Renewals

Vice President of Sales

Scratchpad

Advisor

Whitespace

GTM Advisor

Melio

Led the Accountants segment of Directors, Managers, AEs and SDRs across North America

Fastest growing segment at Melio, supporting channel and direct customers from PLG and sales-led motions

Impacted due to strategy changes in the GTM segment and elimination of ~70% of the direct sales organization

Head Of Sales

Zoom

While at Zoom, I was promoted twice and led many teams across multiple divisions.

Most recently, I led a team of over 70, to scale and grow the SMB East Segment.  

With net new revenue goals in the area of $45M ARR, we focused on acquiring customers, and expanding within existing accounts to leverage the Zoom portfolio of products.  By doing so, we increased ADS, TCV and increased retention across our client base. 

During my time at Zoom, we grew from less than $50M in 2016 to $4B in revenue in 2021, and over 7,000 employees.  I was the first external sales leader hired, and helped to grow the Denver office to 600+. 

I led and collaborated on projects to scale rapidly and get ahead of growth related challenges: territory design & mapping, quota & commission planning, sales enablement, business realignments.  I implemented a variety of sales tools (Leadspace, LinkedIn Navigator, ZoomInfo, Chorus, Outreach, People.ai, Rekener, Clari, Demandbase, among others) with the help of cross functional partnerships.  

▪ Founding member of the Women@Zoom ERG and Zoom Mommas group
▪ Zoom Happy Crew member and Bring Your Kids to Work Day lead
▪ Achieved multiple P-Club and sales accolades, available upon request

Segment Lead: East

Sr. Sales Leader, Commercial

Sales Leader, Mid-Market and Commercial

SendGrid

In this role, we were responsible for acquiring new business, upselling and attaching new portfolio products to our strategic customers.  The sales organization focused on outbound efforts, high value inbound conversion, up-market expansion and new product launches.

I helped found the first DEI committee and ERG at Sendgrid, Prism.  Within sales, I created net new roles including, SDR/BDRs manager and team, Expansion Account Executives and restructured our Strategic Account Executive role.
 
Created new quota/commission model to incentivize the team and achieve business objectives

Reorganized territories and GTM rhythm to focus on strengths and create a rewarding and empowering career path structure.

Director of Sales

Intuit

Demandforce Team: 
Responsible for starting the Demandforce division in the Denver office in 2014.  

Salesforce ISV Team: 
I re-built and restructured the sales team, implemented a new Professional Services offering to increase lead to sale conversion by 453%, and 7% increase of annual revenue target. Increased sales by 78% within the first 2 quarters.

▪ FY14: Intuit Sales Achiever Award

Senior (National) Sales Manager, Division Leader, Salesforce.com for QuickBooks

I strategized with Business Development and Engineering to bring new integrations, medical specialties and partnerships to market. 

I partnered with the Product team to build portals for new EHR/EMR software to increase revenue and GTM opportunity. This included acquiring beta participants and agreements for new integrations. 

I collaborated with our Marketing organization to increase the ROI of events, communications and collateral.  Saw a 10X return on conferences and trade shows.

▪ FY13 President's Club Winner
▪ FY13: 127% to Target 
▪ FY12: 107% to Target

Regional Sales Manager: Medical Division, Demandforce

Managed the entire sales cycle from prospecting, presenting, closing, onboarding and account management as an AE. Cultivated relationships with partners and vendors to network, develop business, and close new business. 

Also, served as a Team Lead in this role, managing an Account Executive as a part of my responsibilities.

Account Executive: Medical Division, Demandforce

VP of Sales | Mom | Investor | Advisor | Connector | Coach

You've stepped into a high-stakes leadership role in tech. Pressure is palpable, targets are aggressive, and your calendar is color-coded chaos.

You're driven, ambitious, and more than committed. 

But behind the scenes?

You're overwhelmed, overextended, second guessing yourself, and quietly wondering: "Is it supposed to feel this hard?"

You don't feel like your cup is full; you feel like you're drowning.

That's where I come in. 

I have 20+ years leading high-performing sales teams at Zoom, Intuit, Outreach, SendGrid, and Melio. 

I'm also a mom, wife, and recovering perfectionist with late-diagnosed ADHD, so I get the messy middle of ambition and growth. 

I know what it's like to carry a number, plan, scale, grow, and lead through uncertainty...all with a brave face when you're unraveling inside.

I coach leaders in tech (many of them new and rising execs) to handle hyper-growth and hyper-pressure environments, while navigating the messy middle of growth; both personally and professionally.

What we work on together:
▪️Building executive presence and unshakeable confidence
▪️Creating clear boundaries without the guilt
▪️Leading with clarity and conviction, not chaos
▪️Redefining success beyond "doing more" and "working harder"

You've got what it takes. Let's help you believe it.

taplio

The Battle

Corey Kossack

Alyson B.

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