Webinar Summary: “Beyond the Résumé – Hiring Great Salespeople for Startups”

Date: Thursday, 20 November 2025, 11:03 AM (GMT+8)

Organizers: GrowWise Solutions and LYC Partners

Speakers:

• Yining Wang, Executive Partner, Sincere Alignment Group Global

• Christian Schneider, CEO, File.ai

• Moderator: Romka (GrowWise Solutions)

Context

GrowWise Solutions and LYC Partners co-hosted this webinar to offer practical advice to founders and early-stage leaders on hiring and enabling great salespeople in startup environments. The session focused on three questions:

1. Why do bad sales hires cost so much more than we think?

2. How can founders recognize red flags when candidates look perfect on paper?

3. What does it take to set the first sales hire up for success and identify true “sales multipliers”?

The session combined perspectives from a serial entrepreneur and investor (Yining Wang), a repeat founder and CEO operating in enterprise AI (Christian Schneider), and a sales advisory and executive search perspective (GrowWise and LYC).

The Cost of Hiring the Wrong Salesperson

The webinar opened with a framing from Romka on why “hiring right” in sales is not just a recruitment question but a strategic decision.

• Research shows that a bad sales hire can cost an organization around USD 850,000 once recruitment, onboarding, salary, slow or missed deals, severance, and rehiring are included.

• The financial cost is only one part. A wrong hire can create what Gallup calls a “culture of contagion”, where underperformance drags down the entire team.

• Unsuccessful hires tend to show 37% more absenteeism, which affects both profitability and morale.

• There is also a brand cost: when a salesperson represents the company poorly in the market, they can damage how prospects experience the product and the organization.

• Sales leaders then spend disproportionate time trying to “fix” an underperformer, instead of focusing on strategy, coaching the rest of the team, and building the future pipeline.

The message to founders was clear: the decision to hire a salesperson is not a quick fix for workload. It is a decision that shapes culture, brand, and growth trajectory.

Speaker Introductions

Yining Wang – Sincere Alignment Group Global

Yining Wang introduced himself as a Swedish–Chinese serial entrepreneur and investor.

• He began his career at Charling Group, one of Sweden’s largest family offices with more than USD 10 billion in assets under management.

• After serving as a public CEO, he co-founded Sincere Alignment Group, a cross-disciplinary ecosystem that combines what he calls the “new economy”:

  • Creative and media innovation

  • AI adoption

  • Existing brands and investors

• Sincere Alignment Group operates as a membership-based platform across roles, working with leading talent in media, creativity, AI solutions, and investment.

• Their work focuses on helping organizations in Europe and Asia make the transformation to more creative-led, AI-enabled growth.

In this webinar, Yining shared from the vantage point of investor, serial founder, and operator in scale-up environments.

Christian Schneider – File.ai

Christian Schneider is the CEO of File.ai, a Series B funded company building a specialized enterprise product for large-scale data processing.

• The company is headquartered in New York with a major office in Singapore, where the business originally started.

• Christian has spent roughly a decade in startups, including early roles at Lazada, combined with prior corporate experience.

• He has raised and deployed significant amounts of capital, built teams across engineering and sales, and navigated complex enterprise sales cycles with global CTOs and COOs.

He described File.ai as a product with a complex enterprise buying motion, where the quality of the sales team has a direct impact on whether the business can successfully navigate multi-stakeholder, high-ticket deals.

Why Sales in Startups Is a Different Game

Selling Something “Not Fully Sellable” Yet

Yining emphasized that startup sales is not the same as sales in an established company:

• In the early stages, the product is still evolving and true product–market fit is not yet there.

• Founders are still discovering their ideal customer profile (ICP) and the right product features.

• That means the first sales hires are often selling something that is not yet easy to sell.

To get to product–market fit, the company needs volume and iteration: many conversations with potential customers and a willingness to learn from each “no.” This is a very different environment from a large organization with:

• A clear ICP

• Stable product features

• Established pipeline and brand recognition

A salesperson who succeeds in a large, well-structured organization may not succeed in a young startup.

Red Flags: When a Strong CV Is Not Enough

In response to the question “What is the biggest red flag that a great-looking sales hire will fail in a startup?”, both speakers pointed beyond the résumé.

1. Lack of Belief in the Product and the Founder’s Vision

Yining’s main red flag is misalignment of belief and ambition:

• The first sales hire should be almost like the founder’s right hand.

• If the person does not believe in the product or the mission as deeply as the founder, the mismatch will show quickly.

• This is especially problematic when the candidate appears perfect on paper: strong SaaS background, great logos on the CV, solid references.

What matters is whether this person is:

• As aspirational and ambitious as the founder.

• Willing to do the hard, unglamorous work: cold calling, experimentation, chasing early adopters.

2. Over-Reliance on Corporate Support Structures

Both Yining and Christian warned about hiring very senior people from large corporations too early:

• These individuals are often used to a full support system:

  • BDR/SDR teams feeding them leads

  • Marketing teams generating demand

  • Mature CRM setups and established playbooks

• In a startup, those structures do not exist yet. The first sales hire must be willing to build the pipeline from scratch, not just work what is handed to them.

If a candidate has not built from zero in many years, they may have forgotten how to hustle, improvise, and adapt.

3. Hiring Too Soon

Christian highlighted timing as an underrated risk:

• The worst cases in his experience were hiring a salesperson too early, before the product is truly ready to be sold by anyone other than the founder.

• Founders often feel the product is “sellable enough,” but when they watch another person try to sell it, they see missteps and feel the urge to take over.

When a founder repeatedly feels compelled to jump into calls and rescue conversations, it is often a sign that:

• The product needs more work.

• The sales motion is not yet repeatable.

• The hire came too early, regardless of the person’s experience.

Early-Stage vs Later-Stage Sales Hires

Christian shared how his view of the “ideal sales profile” changed as File.ai scaled.

Early Days: Young, Coachable, and Adaptable

In the first phase (around five people in the company):

• He naturally gravitated toward younger, hungry, and coachable talent.

• These hires lacked a large Rolodex or long track record of closing big enterprise deals.

• However, they adapted faster to new technology and the realities of a fast-moving AI product, especially in the earlier days when market awareness of AI was lower.

In this phase, the founder must coach closely, and the sales hire must be ready to learn from scratch.

Later Stage: Experienced Operators

As the company grew to 80+ employees:

• Christian started to crave more experience in sales hires.

• At that point, the company had more clarity on product–market fit and a more defined sales cycle.

• More seasoned salespeople could run end-to-end enterprise cycles with confidence and “gravitas” in front of senior stakeholders.

However, even then, he warned against assuming that all experience automatically transfers. A person who constantly refers back to “what worked 10 years ago” may not fit the current product and market reality.

Setting the First Sales Hire Up for Success

In answering “What is the single most important thing founders should do in the first 30 days?”, both speakers focused on enablement and trust.

1. Deep Product Immersion

Christian’s first priority is to sit with the first sales hire and deeply explain the product, with a sales flavor:

• In the beginning, there is often no stable documentation. Product features move so fast that any deck will be outdated within weeks.

• Because of this, the most effective enablement is live and conversational.

• He invites the new hire to join every sales call and mirror how he engages customers:

  • How he explores problems

  • How he positions the product

  • How he responds when things are unclear or objections arise

Over time, the salesperson should tell the founder when they feel ready to run their own calls.

2. Accepting That Documentation Will Lag

Christian pointed out that in fast-moving environments:

• A fully documented, codified process is often impossible to maintain at the beginning.

• This is where founders see if a salesperson can cope with constant change in features, messaging, and target segments.

If someone insists on a stable, fully defined playbook before they act, they may not be a fit for an early-stage environment.

3. Volume × Iteration Mindset

Yining introduced a simple formula for startup sales:

Volume × Iteration = Success

• Each “no” is not just a rejection; it is a data point and a sample in an ongoing experiment.

• Without enough volume, the company cannot learn whether the product and messaging are statistically meaningful or not.

• The right sales hire will see 80% rejection rates not as discouraging, but as part of the learning curve toward product–market fit.

This growth mindset is often more important than previous titles or company names on a résumé.

4. Delegate, Trust, and Allow Mistakes

Yining also stressed a more emotional and leadership point: the real reason you hire sales is to scale.

• If the founder keeps stepping in on every call and closes every deal, they are not truly scaling.

• The first sales hire will never be as good as the founder at selling the product in the beginning.

• The only way for this person to grow into a multiplier is for the founder to:

  • Let them write their own scripts

  • Let them make mistakes

  • Start them with smaller or lower-stakes clients if needed

  • Keep the primary focus on learning and iteration, not perfection

Otherwise, the hire becomes just “an extra pair of hands,” not a real sales leader who can run in parallel while the founder focuses on product and company-building.

From Sales Operator to Sales Multiplier

When asked how to distinguish a “sales multiplier” from a regular operator, Yining highlighted ownership and entrepreneurial mindset:

• A multiplier behaves almost like a “sales entrepreneur” or intrapreneur inside the business.

• They do not wait passively for leads, instructions, or marketing support. Instead, they:

  • Build their own multi-channel approach (outbound, social, referrals, events).

  • Proactively research and identify target customers.

  • Take responsibility for their own pipeline and learning.

The only reason such a person is not founding their own startup may be that they have a different skill set or risk profile, but their energy and ownership level are similar.

Christian added that as the company transitions from 5 to 20 employees and beyond:

• A true multiplier is the one who can translate founder-led success into a repeatable motion, tracking funnels, running structured experiments, and helping onboard future sales hires.

• They move the organization from “heroic individual efforts” to systematic, measurable growth.