StartWise 

Transforming Careers and Businesses with Strategic Coaching and Consulting

Fueling professional transformations at StartWise, where we specialize in executive career coaching and Go-To-Market (GTM) consulting. With nearly two decades of hands-on expertise, we deliver measurable results through evidence-based methodologies. Let's elevate your career or business to new heights!

   - Specialized in Executive Career Coaching, offering transformative services such as career coaching, layoff navigation, executive onboarding, extended leave guidance, professional branding, and promotion planning.
   - GTM/Sales and Customer Success Consulting, providing business advising and coaching for founders, sales coaching, customer success coaching, and facilitating strategic change and organizational transformation.

Services:
1. Executive Career Coaching:
   - Career transformation coaching
   - Navigating layoffs and securing new employment
   - 30-60-90 day executive onboarding coaching and plan
   - Guidance on extended leaves (maternity leave, elder care, sabbatical)
   - Professional branding and promotion planning
   - Specialized coaching for women in tech and high-growth industries

2. GTM/Sales and Customer Success Consulting:
   - Business advising and coaching for new and aspiring founders
   - Tailored sales coaching to boost revenue
   - Customer Success coaching for enhanced client satisfaction and retention
   - Strategic change and organizational transformation services

Skills:
Customer Retention | Go-to-Market Strategy

Open to networking and exploring collaboration opportunities in career coaching and GTM strategy.

Founder and Principal Coach

Somersault Innovation

I teach sales teams how to apply design thinking—the creative problem-solving methodology used in innovation— to sales and customer success.

Sales Performance and Design Thinking Coach, EU & NA

The Alchemy Project

Transforming youth potential into leadership potential through entrepreneurship

The Alchemy Project is a program designed to help high potential at risk youth acquire the valuable skills and experiences necessary for the future of work through startup competition and career simulations.

Board Member

Revioly

Advisory Board Member

Salsify

Vice President, Customer Success and Strategic Partnerships, Retail

Amperity

Lead the Enterprise Sales, Sales Operations, Sales Enablement and overall sales GTM. Work in tight partnership with cross-functional leaders in Marketing, Product and Client Success to drive strategy and GTM. 

Report to CEO.

Vice President of Sales

Bazaarvoice

Led Sales, Client Success & overall GTM strategy for Bazaarvoice's Retail Division - the cornerstone of the company's overall partner network.  My team’s purview included business development, hunter/farmer sales, and client success.

The mission of the division was rooted in designing symbiotic partnerships between Bazaarvoice and our global retail clients in order to drive universal business value. 

A few key accomplishments:
  
- Retail Business Development Channel became second largest contributor of overall pipeline in the business under my leadership, generating millions of $'s in qualified pipe YoY

- Consistently exceeded net portfolio growth targets by minimizing dollars churned (sub 5% across division) while maximizing acquisitions and expansions (200+% to plan)

- Division was consistently the highest performing division across the business against KPI's, NPS and quota YoY under my leadership

Vice President, Sales and Customer Success/ General Manager, Retail Division

Named CEO MVP of the Year two years in a row for leadership, strategic vision, and consistent overachievement of business goals.

Managing Director, Global Retail

TrialPay

One of the first employees at TrialPay - a leader in the alternative payment space (ultimately acquired by Visa). 

Responsible for leading the team that sold, launched and expanded our top 100 most strategic partnerships. Consistently led team to exceed sales and revenue goals upwards of 150% and saw YOY sales growth of 40%.  Key player in building TrailPay's European business and ultimate launch of Berlin office.

Director, Global Account Management (acquired by Visa)

Jaqua Beauty, Inc.

Lead prospecting and market penetration of Jaqua Beauty into multiple national retailers, including securing new distribution channels through retailers like ULTA, Nordstrom, QVC, and Sephora.

Accounts managed experienced consistent YoY growth of up to 60%. Averaged 46% net profit increase for managed accounts yielding the highest profit on the sales team. Designed and implemented online marketing and e-commerce programs that resulted in a 254% increase in online membership and an AOV increase of 71% per customer.

Senior Director, Sales

tarte inc.

One of the first 6 team members at tarte inc.

Helped expand Tarte, Inc. from 20 retail locations in October 2002 to over 60 locations, including launching the brand in major national retailers such as Sephora, Nordstrom, and QVC.
Managed 35+ sales associates across 30 retail accounts throughout the Eastern United States. Established individual sales goals, reviewed performance, and managed compensation. Deeply involved in product development and go-to-market strategy for new products.

Senior Account Executive, Eastern Region

Sara is a dedicated and experienced executive coach and a 20 year technology leader in both Sales and Customer Success. Leveraging her leadership skills, Sara has helped a number of early stage and established technology companies grow rapidly over her 20 year career.  

In addition to building successful startups, Sara has supported many people in their professional journeys, often navigate intense moments of change including coming back to work after an extended leave, starting their own businesses or leveling up in leadership.

Sara is a mom and a first generation college graduate and first generation corporate professional. She has a passion for supporting women and first generation professionals on their unique journeys.  

At her company, StartWise, Sara recognizes that our personal and professional journeys are not linear, always heading "up and to the right". Our careers often have moments of change and transition.  Sara and StartWise strive to help professionals navigate these moments by offering various coaching programs and packages designed to allow professionals to capitalize on change.

If you want to ensure you take ownership over your career, StartWise is for you!

AI "work slop" and the problem with zero-sum thinking — and the path to fixing it.

AI work slop is the latest trend to emerge in the AI + GPT adoption journey.

Essentially, it captures the phenomenon where quality is being compromised for the perception of speed when using a GPT.

In many instances, people are starting to discover that fast does not always mean better — and they’re seeing work quality suffer, requiring significant time to fix or redo the AI’s output.

Enter the term “work slop.”

It swings the pendulum to the opposite extreme — seemingly debunking the value of AI tools because of the cleanup required.

But this is classic zero-sum thinking — the belief that if one idea is flawed, the opposite must be true.

In reality, the truth is somewhere in the middle.

But here’s the hard part: landing in that middle ground requires personal accountability.

It asks us to take an active role in what we’re creating and producing — even when we were promised the “easy button.”

The real opportunity with AI isn’t speed for speed’s sake — it’s leverage.

But leverage only works if we hold ourselves accountable for the outcomes, not just the output.

AI is a powerful thought partner, not an autopilot.

When we slow down enough to guide it, question it, and refine it, we turn “work slop” into real, lasting impact.

The easy button was never the point.

The point is using these tools to raise the standard of what we create — and owning the results.

As a leader, it is your role to ensure your team is taking the right steps to use AI to amplify their ideas, increasing efficiency without sacrificing quality.  Since no one likes "slop".

Sara Gupta (She/Her)

I help high-achieving executives navigate complexity, expand their influence, and gain the visibility they need to perform at the next level | Founder, StartWise | Former Tech VP | ICF-Certified Executive Coach |

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