It IS a Dilemma — Remote vs. Hybrid vs. In-Person Sales Leadership

Henning Schwinum
4 min readDec 2, 2023

How Do You Make the Right Choice When Hiring as a Business Owner?

“A dilemma is a problem offering two or more possibilities, none of which is unambiguously acceptable or preferable.”

Definition of Dilemma

In a world reshaped by the pandemic, the realm of sales leadership has been thrust into a profound dilemma — a tug-of-war between remote, hybrid, and traditional in-person models. This seismic shift has not only

(1) altered the dynamics of how buyers and sellers interact. It has also prompted a

(2) rapid evolution in the expectations and methodologies of sales leaders, and what

(3) factors business owners might want to consider when facing the hiring dilemma.

This 1–2–3 scenario is deeply interconnected.

Let’s break this down: Recent studies have revealed a staggering statistic: less than 2% of sales leaders perceive the changes in buying and selling behavior as temporary. This sentiment underscores a fundamental truth — the landscape of sales has irrevocably transformed.

One of the pivotal changes catalyzed by the pandemic is the burgeoning divide between remote buyers and sellers. Business buyers, influenced by their consumer purchasing experiences, have swiftly elevated their expectations from B2B sellers. Consequently, the onus lies heavily on sales leaders to adapt, innovate, and recalibrate their strategies, teams, processes, and technology.

Re. (1): The pandemic forced a global dispersion of selling teams, hastening the adoption of virtual selling channels. However, this transition hasn’t been without challenges. Some studies indicate that sales productivity has dipped by 20% since the pandemic’s onset, as leaders grapple with managing remote teams and aligning measurement metrics with a dispersed workforce.

The resounding consensus among experts is clear — virtual selling represents the future commercial model. The above response to the pandemic has propelled sales organizations beyond a point of return. Remote selling channels and digital buying practices are poised to redefine the sales landscape, necessitating an overhaul of traditional practices.

Re. (2): To navigate this new landscape, today’s Sales Leaders have to embrace these five actionable strategies:

1. Speed: Accelerate Communication and Responsiveness

Remote settings demand swift and inclusive communication. Sales teams need transparent information to pivot quickly and make informed decisions. The urgency to address customer queries in minutes or hours, not days, underscores the importance of agility in response.

2. Tools: Equip Sales Teams for Remote Excellence

Equipping sales teams with essential tools for remote operations is foundational. The pandemic has underscored the necessity of unified communications, collaboration platforms, and sales enablement tools. As face-to-face interactions diminish, investing in remote capabilities becomes imperative.

3. Visibility: Gain Insights into Buyer and Seller Activity

Enhancing visibility into buyer behavior and sales activity is critical. Improved data access empowers managers to make informed decisions, coach effectively, and guide remote teams. Better control over engagement data is pivotal in a post-COVID marketplace.

4. Renewed Focus: Prioritize Relationship Building and Pipeline Growth

With uncertain demand, doubling down on relationship building and pipeline management becomes paramount. Identifying and nurturing valuable opportunities while leveraging sales AI for lead qualification becomes the bedrock of success.

5. New Sales Plays: Redesign the Playbook for Virtual Selling

The disparity between traditional field selling and digital buying necessitates a revamped playbook. Sales organizations must adapt strategies, redefine roles, and equip teams with the skills required for virtual interactions.

Re. (3): When a business owner navigates the labyrinth of choosing between remote, hybrid, or in-person hiring for sales leadership roles, several crucial factors come into play:

  • Considering the talent pool becomes pivotal. Remote roles expand the possibilities by accessing a global talent pool, whereas in-person roles might be confined to a local or regional spectrum.
  • Evaluate the job requirements because some roles demanding constant collaboration may benefit from in-person settings, while positions focusing on individual tasks might be suitable for remote work.
  • Assess the technological needs for the role, as well as the companies’ ability to deliver. Remote and hybrid work require robust tech support for seamless communication and collaboration, whereas in-person roles might have different infrastructure demands.
  • Understand the preferences and productivity of your future hire. Some employees excel in remote settings, while others thrive in a structured in-person environment. Also understand their flexibility to come on-site if necessary.
  • Evaluate the financials. Remote work often reduces overhead costs, such as office space, but might require investments in remote infrastructure.
  • Consider the impact on company culture and team dynamics. In-person work might foster stronger initial bonds, while remote setups require intentional efforts to maintain a cohesive team culture.
  • Speed in filling the role is another significant consideration. Remote hiring often accelerates this process due to a broader reach and quicker evaluations, while in-person roles might involve longer lead times due to location-specific constraints, or the need for the talent to relocate first.
  • Faster onboarding is an advantage in remote or hybrid setups, leveraging digital tools for efficient orientation, although in-person roles might foster quicker team integration due to physical proximity and face-to-face interactions.

Assessing the balance between these factors becomes crucial in determining the most suitable hiring approach aligned with the company’s culture, goals, and the nature of the sales leadership role. Let’s go and tackle the dilemma.

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Photo by Anne Gosewehr

Originally published at https://www.vendux.org on December 2, 2023.

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Henning Schwinum

Chief Evangelist for Interim & Fractional Sales Leadership