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

Chuck Brotman

Blueprint Expansion

VP of Sales & Co-Founder

GTMnow

GTM Expert Contributor

GTMfund

Limited Partner

Pavilion

Executive Member

Metagrove Ventures

Mentor

Turazo

Sales Advisor

Skaled Consulting

Senior Consultant

PeopleGrove

PeopleGrove helps foster meaningful relationships between students and alumni at scale.  This expands opportunities for success before, during, and after the college experience.

I built out and managed the sales team to support expanded go-to-market initiatives in North America and beyond.  I met so many remarkable individuals during my tenure who taught me the importance of promoting expanding social equity and access within higher education - for students, employers, and our country at large.

VP of Sales

KeepTruckin

KeepTruckin offers a modern, end-to-end fleet management solution.

In my tenure, I achieved nearly 3x the 2017 plan number and grew cumulative ARR 80x in the last 12 months with the company.
I built out the sales management team, spanning SDR, SMB, Mid-Market, Enterprise, and Partnerships, and oversaw 6x growth of the sales organization and the launch of a new office in Nashville.
I implemented business management cadences, refined overall sales process for each segment, and drove process integration across geographically-dispersed teams.

ON24

My team was responsible for introduction of ON24 solutions to growth-focused Mid-Market companies.  We worked in industries spanning B2B Tech, Accounting, Consulting, Insurance, Financial Services, and Healthcare.

VP, Mid-Market Sales

VP, SMB & Mid-Market Sales West

I managed ON24 Channels and Alliances across North America and LATAM.  My teams drove new and expansion revenue growth across segments spanning Telco / CSPs, Agency, ITO / BPOs, Technology, and regional Resellers and VARs.

Vice President, Channels and Alliances

Director, Channels

Built out and managed sales engineering team to support ON24's global sales organization.

Director, Sales Engineering

Supported Sales team that grew from 6 to 20 salespeople over 2 years.  Handled RFP / RFI responses and key product demos and prototypes.  Worked closely with Professional Services, Engineering, and Product teams.

Sr. Sales Engineer

Sales, Marketing, CS, & Leadership Recruiting | Blueprint Expansion aka gtmrecruiter.com

We help early and mid-stage companies recruit exceptional go-to-market talent (that others often miss).

These articles cover my thinking on various topics
https://www.linkedin.com/in/cbrotman/recent-activity/posts/

Here are six core beliefs:

1. We need to do a better job at promoting career opportunities for underrepresented groups in the broadest possible sense.  DEI professionals often get this wrong.  We need to change the way we source, engage, and onboard talent from all walks of life.  If we do so, companies will perform better.

2. Cronyism is a problem in tech hiring.  We need to get more comfortable hiring strangers and getting outside our personal networks.  

3. If you hire "from the gut," you may not have a hiring process. Without a process, you cannot scale.

4. It's not a virtue to "fire fast" - and it's never been a virtue.  Companies need to do a better job at on-boarding their new hires.

5. Personal branding evangelism has pyramid-scheme like features.  Worrying about your personal brand before you develop key skills is putting the cart before the horse. 

6. Be wary of remote work evangelism. It may be creating the conditions for the outsourcing of everything.  Sitting on video calls all day is dystopian.  I like remote work, but it's had an adverse impact on our communities, mental health and talent skills development. It's a very complicated topic.


email: chuck@blueprintexpansion.com
phone or text: 415.720.7710

In hiring, guess what?  

A. Great candidates ask great questions.  
B. Mediocre ones ask bad ones.  

It's never been truer than in 2025.  This is how you show your own processing power in real time, eye-to-eye.
Can you think, challenge, and interpret without an LLM holding your hand?

The best candidates do this before they start asking questions:

Preparation
 ➤ They show up for an interview understanding the company’s value prop, mission, and vision (even when they were recruited by someone else.  Time is valuable!)
 ➤ They research investors, customers, staff, location, and basic news coverage.
 ➤ They avoid asking anything they could answer thenselves with a 5-second LLM prompt.

Presence
 ➤ They listen closely, they are no just waiting to talk.
 ➤ They spot the real challenges, tensions, and gaps behind what’s being said, and get clarity by asking the right questions.
 ➤ They ask follow up ones when needed to incomplete or vague answers.
 ➤ They’re willing to ask hard questions: direct but diplomatically.

Strategy
 ➤ Their questions shift based on who they’re speaking with and where they are in the process. Much like the hiring company, they have their own structured assessment process and gates they use to dictate how they make decisions whether they'll invest more time in an interview cycle.

In a world where anyone can sound polished and prepared asynchronously, great LIVE questions are one of the strongest signals how you think and execution.  

Be ready to ask them.

#interviewing
#interviewquestions

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The Battle

Corey Kossack

Chuck Brotman

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taplio

The Battle

Corey Kossack

Chuck Brotman

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Chuck Brotman's LinkedIn Performance

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Performance ScoreChuck Brotman's LinkedIn Performance