Looking back: April 2026
When enterprise selling moved remote in 2020, a lot of what had worked in the pre-2020 era had to be rebuilt. Some of the rebuilding produced better motions than existed before. Some of it produced worse ones. Understanding which is which has been clarifying in retrospect.
What Got Harder
Reading the room.
In-person meetings transmitted dozens of small signals — how the champion was reacting to the skeptic, who was checking their phone, whether the energy in the room was with you or against you. On video, most of those signals disappeared. Sellers who relied heavily on reading the room had to rebuild their craft around the narrower bandwidth of video meetings.
The best sellers found ways to compensate — asking more direct questions, checking in explicitly with specific stakeholders, structuring the meeting to draw out reactions that would have been spontaneous in person. The lesser sellers kept expecting the signals to come through and missed them.
The hallway conversation.
In-person meetings had a structure where the formal meeting was 70% of the value and the 30% that happened in hallways, over coffee, walking to the parking lot was often where the real progress happened. Those informal moments disappeared almost entirely in remote selling.
The adaptation was to engineer equivalents: specific one-on-one video calls, separate calendar time for off-record conversations, use of messaging platforms for between-meeting dialogue. These worked, partially. The equivalents never fully matched the spontaneous-hallway version.
Building trust with people you haven’t met in person.
Some of this wasn’t obvious until later. Trust can be built on video — but the depth and durability of that trust, in retrospect, seems shallower than the in-person equivalent. Relationships formed entirely remote during 2020-2022 often proved less resilient to difficulty than relationships with equivalent touch count that included some in-person contact.
The lesson: the high-bandwidth modalities build relationships faster than the low-bandwidth ones. When everything was low-bandwidth, the relationships still formed, but with shallower foundations.
What Got Easier
Access.
Getting a meeting with a senior executive became dramatically easier in 2020. The logistics overhead of in-person meetings — flights, parking, calendar blocks — had constrained how many meetings senior people could take. When all meetings became 30-minute video calls, senior executives could take 6 to 10 meetings a day where they previously took 3 to 5.
This meaningfully expanded the pool of possible conversations for many sellers. Cold outreach to executives became more productive because the calendar constraint had eased. Existing relationships became easier to maintain because a quick video check-in was lower-friction than scheduling a lunch.
Geographic reach.
Regional sellers who could previously only cover their geography could now work across regions. Enterprise deals in cities the rep had never visited became viable. This expanded the effective market for many sellers and compressed the advantage of locally-based competitors.
Parallel engagement across buying committees.
In-person selling was almost always sequential — you had meetings with specific stakeholders in specific sequence, and the timeline was governed by travel logistics. Remote selling let sellers run parallel engagement across multiple stakeholders simultaneously. The CTO call could happen Tuesday, the CFO call Wednesday, the operations call Thursday — with all three feeding into a unified internal pipeline of the deal.
This actually compressed some deal cycles, especially for deals where multi-threading was the primary constraint.
What Became a Permanent Mixed Bag
Discovery.
Discovery calls got more efficient (no travel time, tighter agendas) and less rich (fewer side conversations, less whiteboard collaboration). The net effect varied by industry and deal type. Complex, multi-stakeholder discovery still benefited from in-person intensity. Simpler, single-stakeholder discovery was often better on video.
Closing.
Closing a significant deal via video remained awkward for years. Something about the final steps — the handshake equivalent, the moment of commitment — didn’t transmit cleanly over the video medium. Many sellers found that they could do 80% of a deal remotely but wanted the final stages in person.
What I’d Tell Anyone Rebuilding
If you’re optimizing a sales motion in 2026, the remote-selling lessons are still live:
- Don’t fight the hybrid equilibrium. Engineer it.
- High-bandwidth modalities (in-person, long-form video, workshops) build deeper relationships faster. Use them strategically.
- Low-bandwidth modalities (email, chat, short video) scale broader but shallower. Use them for volume.
- Sequence deliberately. Use remote for early, in-person for inflection points, remote for execution.
The sellers doing the best work now are the ones who’ve internalized this layering. Not remote-first. Not in-person-first. Deliberate-sequencing.
The remote shift didn’t kill in-person selling and it didn’t replace it. It reshaped the hierarchy of which modalities do which work. Five years in, the sellers who’ve digested that reshaping have better motions than existed before. The ones who haven’t are still nostalgic for 2019 or still overcommitted to 2020.
Neither nostalgia nor overcommitment serves. The hybrid reality is the stable one now. Work from there.